; TeX output 1996.05.03:1603ObM2 y] ANG cmbx12AX*(tMOTc EX:AzMacroPuackagezfor+'Tuyp=esettingzChemicalStructuralFaGormulasGC|25ObM2C'TNH cmbx12TCon8tents?]'#"V cmbx101 'In9troQductionsv7 '1.1#'Backgrounds ʍ...........................................x7 '1.2#'TheUUNameofthePackqage....................................x8 '1.3#'Requirementsq\...........................................x8]'2 'TheTConstructionofX̟ \MٖT<8E3sX- 9 '2.1#'Overviewk.............................................x9 '2.2#'GeneralUUConventions.......................................x9#'2.2.1C'UserUUCommandsforSpGeci edUseandforGeneralUseBF................x9#'2.2.2C'SuxUUandArgumentsH..................................x10'3 'Six-Mem9bQeredTCarbocycles"o13 '3.1#'DrawingUUBenzeneDerivqatives..................................x13#'3.1.1C'V*erticalUUFormsofBenzeneDerivqativesb.........................x13#'3.1.2C'HorizontalUUF*ormsofBenzeneDerivqatives~........................x15 '3.2#'DrawingUUCyclohexaneDerivqatives................................x15#'3.2.1C'V*erticalUUFormsofCyclohexaneDerivqatives降.......................x15#'3.2.2C'HorizontalUUF*ormsofCyclohexaneDerivqatives.....................x17'4 'CarbQocyclesTwithF usedSix-Mem9bQeredRingsǭ19 '4.1#'DrawingUUNaphthaleneDerivqatives................................x19#'4.1.1C'V*erticalUUFormsofNaphthaleneDerivqatives降.......................x19#'4.1.2C'HorizontalUUF*ormsofNaphthaleneDerivqatives.....................x21 '4.2#'DrawingUUT*etralineDerivqativesۻ..................................x21#'4.2.1C'V*erticalUUFormsofTetralineDerivqatives).........................x21#'4.2.2C'HorizontalUUF*ormsofTetralineDerivqatives (.......................x22 '4.3#'DrawingUUDecalineDerivqatives-..................................x23#'4.3.1C'V*erticalUUFormsofDecalineDerivqativesF.........................x23#'4.3.2C'HorizontalUUF*ormsofDecalineDerivqatives).......................x24'5 'F usedTTricyclicCarbQocyclesandSteroids*27 '5.1#'DrawingUUAnthraceneDerivqatives................................x27#'5.1.1C'CommandUUforSpGeci edUse...............................x27#'5.1.2C'CommandUUforGeneralUse...............................x28 '5.2#'DrawingUUPhenanthreneDerivqatives...............................x30#'5.2.1C'CommandUUforSpGeci edUse...............................x30#'5.2.2C'CommandUUforGeneralUse...............................x31 '5.3#'DrawingUUSteroidDerivqatives"ލ...................................x32KF3ObM'4p;"p0J cmsl10CONTENTS'fe>|2 '6 'Fiv9e-TorLower-MembQeredCarbocyclesŁ37 ]卍 '6.1#'DrawingUUFive-MembGeredCarbocycles0..............................x37#'6.1.1C'V*erticalUUFormsߍ......................................x37#'6.1.2C'HorizontalUUF*ormsF.....................................x38 '6.2#'DrawingUUF*our-MembGeredCarbocyclesX.............................x39 '6.3#'DrawingUUThree-MembGeredHeterocycles⍍............................x40 '6.4#'DrawingUUIndaneDerivqatives...................................x42#'6.4.1C'V*erticalUUFormsofIndanes"ɍ................................x42#'6.4.2C'HorizontalUUF*ormsofIndanes?0...............................x44G)'7 'Six-Mem9bQeredTHeterocycles|47 '7.1#'DrawingUUV*erticalFormsofSix-MembGeredHeterocycles򍍑....................x47#'7.1.1C'CommandsUUforSpGeci edUseb..............................x47#'7.1.2C'CommandsUUforGeneralUseO...............................x49 '7.2#'DrawingUUHorizontalF*ormsofSix-MembGeredHeterocyclesn..................x52#'7.2.1C'CommandsUUforSpGeci edUseb..............................x52#'7.2.2C'CommandsUUforGeneralUseO...............................x53'8 'Fiv9e-TorLower-MembQeredHeterocycles\57 '8.1#'DrawingUUV*erticalFormsofFive-MembGeredUUHeterocyclesy...................x57#'8.1.1C'CommandsUUforSpGeci edUseb..............................x57#'8.1.2C'CommandsUUforGeneralUseO...............................x59 '8.2#'DrawingUUHorizontalF*ormsofFive-MembGeredHeterocycles..................x61#'8.2.1C'CommandsUUforSpGeci edUseb..............................x61#'8.2.2C'CommandsUUforGeneralUseO...............................x63 '8.3#'DrawingUUF*our-MembGeredHeterocyclesTv.............................x64 '8.4#'DrawingUUThree-MembGeredHeterocycles⍍............................x65'9 'HeteroQcyclesTwithF usedSix-Mem9beredRingsD67 '9.1#'DrawingUUV*erticalFormsxF.....................................x67#'9.1.1C'CommandsUUforSpGeci edUseb..............................x67#'9.1.2C'CommandsUUforGeneralUseO...............................x69 '9.2#'DrawingUUHorizontalF*orms....................................x71#'9.2.1C'CommandsUUforSpGeci edUseb..............................x71#'9.2.2C'CommandsUUforGeneralUseO...............................x73'10 'HeteroQcyclesTwithF usedSix-andFiv9e-MemberedTRings%75 '10.1#'DrawingUUV*erticalFormsxF.....................................x75#'10.1.1C'CommandsUUforSpGeci edUseb..............................x75#'10.1.2C'CommandsUUforGeneralUseO...............................x78 '10.2#'DrawingUUHorizontalF*orms....................................x79#'10.2.1C'CommandsUUforSpGeci edUseb..............................x79#'10.2.2C'CommandsUUforGeneralUseO...............................x82'11 'BuildingTBloQc9ks]c85 '11.1#'Six-MembGeredUUBlocksT......................................x85 '11.2#'Five-MembGeredUUBlocks10......................................x86 '11.3#'SettingUULoGcantNumbGersэ.....................................x87.ObM'CONTENTSp;5'fe>|2 '12 'F urtherTCyclicCompQounds$o89 '12.1#'DrawingUUChairF*ormofCylohexane?,...............................x89 '12.2#'DrawingUUBicyclo[2.2.1]heptane..................................x90 '12.3#'DrawingUUAdamantaneDerivqatives n................................x93 '12.4#'DrawingUUF*uranosesandPyranosesh...............................x94'13 'AliphaticTCompQounds>97 '13.1#'DrawingUUT*etrahedralUnitsFn...................................x97 '13.2#'DrawingUUT*rigonalUnits1(.....................................x98 '13.3#'DrawingUUEthyleneDerivqatives..................................x99 '13.4#'DrawingUUCon gurations퍍..................................... x101'14 'Com9biningTstructures9F103 '14.1#'GeneralUURemarksK......................................... x103#'14.1.1C'CoGordinatesUUofthePictureEnvironment........................ x103#'14.1.2C'ReferenceUUPointsandInnerOrigins........................... x103#'14.1.3C'SettingUUCoGordinatesM................................... x104 '14.2#'CombinationUUofMacrosThroughaBond0؍............................ x105 '14.3#'UsingUUBuildingBloGcks-...................................... x107'15 'LargeTSubstituen9tsHQ|113 '15.1#'BasicUUIdeas1d............................................ x113 '15.2#'NestedUUSubstituentsȍ....................................... x115'A 'ListTofCommandsJ}121 'A.1#'aliphat.styc/............................................. x121 'A.2#'carom.sty?............................................. x121 'A.3#'lowcycle.sty+............................................ x122 'A.4#'ccycle.sty............................................. x122 'A.5#'hetarom.sty............................................ x123 'A.6#'hetaromh.styʍ........................................... x125 'A.7#'hcycle.sty............................................. x126 'A.8#'chemstr.styx............................................ x127 'A.9#'loGcant.styF............................................. x127gObM'6p;CONTENTS'fe>|2ObM2U΍'UNq cmbx12UChapter 12K'TIn8tro duction:K'1.1" Backgroundst'The`textformatterTU>'ExXdevelopGedbyKnuth[1]iswidelyusedinpreparingmanuscriptsofscienti c 'papGers(.andinthetypesettingprocessesofseveralscienti cjournalsandbGooks(.(forarecentexample,'seeJ[2]).nKInparticular,LL5ffٓRcmr7A͉TU>'ExX,aJTU>'EXmacropackqagethatwasreleasedbyLampGort[3],Lhasexpandedthe'soGcietyUUofTU>'ExXusersbecauseofplainness. K 'Since!thebGeginningofitshistory*,TU>'ExX(L5ffA͉TU>'EX)placesspGecialemphasisonmathematicstypesetting.'Hence,wit{hasbGeenacceptedbyscientistswhohavetowritemathematicequations.LIncontrast,wthe'TU>'ExX/L5ffA͉TU>'EXtypGesettingislesspopularinchemistrythaninmathematicsandother elds.Oneofthe'reasonsUUisthattherearefewTU>'ExX/L5ffA͉TU>'EXUUutilitiesfortypGesettingchemicalstructuraldiagrams. 'AlthoughL5ffA͉TU>'ExXprovidesuswithapictureenviromentfordrawingsimple gures,litsoriginalcom-'mandsJaresoprimitiveastobGedirectlyappliedtothedrawingofstructuralformulas.Hence, the'commandsUUshouldbGecombinedtoproducemoreconvenientUUmacros. 'Pioneering^SworksbyHaasandO'Kane[4]andbyRamek[5]haveprovidedsuchmacrosthatallowusto'typGesetstructuralformulas.FThemacrosoftheformerapproachareavqailableinthepublicdomain,bGeing'named[ChemTU>'ExX.jAlthoughtheyareeasiertousethantheoriginalpictureenvironment[ofL5ffA͉TU>'EX,]they'stillXhavesomeitemstobGeimproved.{ThemostinconvenientitemistheincapabilityofaccommoGdating'10yormoresubstituents.RItstemsfromthefactthatoneargumentisusedtoassignonesubstituent(or'oneob8ject)ineachofthemacrosofHaas-O'kqane'sapproach.Notethatthedirectusageofarguments'enables\usonlytoassign9orlesssubstituents,^bGecauseamacroinTU>'ExX/L5ffA͉TU>'EX\iscapableoftaking9or'lessUUarguments. 'F*orUUexample,the$'ExX'fe>|2  `u3.'It!isdicultwithoutareferencemanualtodi erentiatebGetweenoneargumentforspGecifyingbonds 'andUUanotherargumentforspGecifyingsubstituents.' `u4.'Thetargument`Q'YisselectedtoshownomoGdi cationbecausethischaracterishardlyeverfoundin'amchemicalstructureformula.However,stheuseofthischaractermaybGecomenecessaryinfuture.'SuchUUexplicitdescriptionof`noaction'shouldbGeavoided.Oh 'Asaresult,Ȟtheformatsandcontentsofargumentsaredi erentfromoneargumenttoanotherand'from onemacrotoanothersuchthatatypicalTU>'ExXuser,asecretaryorachemistauthor,maygiveupto'memorizesuchmacros. Hence,moresystematicandconvenientmacrosaredesirableinordertospread'theUUtypGesettingofchemicalstructureswithTU>'ExX/L5ffA͉TU>'EX. 'ThepresentpackqageXMTU>'ExXinvolvesconvenientmacrosfortypGesettingchemicalstructuralformulas'[6]. These2macrosarebasedontechniquesinwhichinnerbGonds,isubstituentsandhetero-atomsona'skeletonareseparatelyassignedwithoutsuchlimitationofnumbGers.%ThepackqageXMTU>'ExX^1=willbGea'moreUUversatiletoGolifitiscoupledwiththemacroswhichtheauthorhasreleasedinabGookUU[7]. '1.2" TheffNameofthePackage'Thefword`chemistry'stemsfromanArabianroGot`alchemy',jwhichis,jinturn,consideredtocomefrom'Greek,r b> cmmi10[D 1.bThelXMlofthenameXMTU>'ExXisanuppGercaseformof[.bThisconformstoaruleof'coinage,UUbGecausethenameTU>'ExXisalsoawordofGreekorigin(!). 'ThempronuncialtionofXMTU>'ExXisrecommendedtobGe`kh#pymtekh',)inwhichthe`kh'soundmaybGe'a7MRussian`kh'ormoresimplyanEnglish`k'andthesymbGol`y'isexpectedtobepronouncedlikea'GermanUU`Gu'. 'The /logoXMTU>'ExXisde nedasbGeingeitherofthefollowingstatements.UThesecondonehasbGeen'adoptedUUthroughoutthepresentmanual.^2'%%%XyMTeX?Logo:Definition1%%%'\newcount\TestCount'\def\XyM{\ifnum\fam=-1\relax\fam=0\relax\fi\TestCount=\fam%'X\kern-.30em\smash{\raise.50ex\hbox{$\fam\TestCount\Upsilon$}}%'\kern-.30em{M}}'\def\XyMTeX{\XyM\kern-.1em\TeX}'%%%XyMTeX?Logo:Definition2%%%'\def\UPSILON{\char'7}'\def\XyM{X\kern-.30em\smash{\raise.50ex\hbox{\UPSILON}}\kern-.30em{M}}'\def\XyMTeX{\XyM\kern-.1em\TeX}'WhenvFsucharaisedGreekletterasthe`'isnotavqailable,XMTU>'ExXmaybGereferredtobytyping`XyMTeX'. '1.3" Requirements'TheԬmacropackqageXMTU>'ExXrunswithinL5ffA͉TU>'EX,sinceitisbasedonthepictureenvironmentԬofL5ffA͉TU>'EX.'BigL5ffA͉TU>'ExXUUshouldbGeusedbecauseXMTU>'ExXrequiresaconsiderableresourceofmemory*. 'Italsorequiresanoption le`epic.sty'developGedbyPoGdar[8],becausethe\dottedlinecommandof'epicisusedinthemacros.ZF*orexample,amanuscript leshouldbGeginwithsuchastatementasfollows:'\documentstyle[epic,carom,hetarom]{article}'whereinUU`carom'and`hetarom'arestyle lescontainedinthepackqageXMTU>'ExX.'6ffH J= "5-:Aacmr61L|{Ycmr8TheXpresenÎtmanualonXs0GM&cTAEMXisnotp "5-:2LDe nition512isadoptedinthemanÎualb'ExXcontainsstyle leslistedinT*able2.1andtheirdoGcuments.LThestyle le`chemstr.sty'isthe 'basic lethatisautomaticallyreadwithinanyotherstyle leofXMTU>'ExX.Q=Itcontainsmacrosforinternal'use,1e.g.,common(commandsforbGond-settingandatom-setting.bTheotherstyle lescontainmacrosfor'users.#cT*ableUU2.1:qStyleFilesofXMTU>'ExXR@)'L͉ffmPfdstyleUUname5includedUUfunctionsffmPaliphat.styKNBmacrosUUfordrawingaliphaticcompGounds carom.styKNBmacroskfordrawingverticalandhorizontaltypGesofcarbocyclicKNBcompGoundslowcycle.styKNBmacrosUUfordrawing ve-or-less-membGeredcarbocyles.ccycle.styKNBmacrosUUfordrawingbicycliccompGoundsetc.hetarom.styKNBmacrosUUfordrawingverticaltypGesofheterocycliccompoundshetaromh.styKNBmacrosUUfordrawinghorizontaltypGesofheterocycliccompoundshcycle.styKNBmacrosUUfordrawingpyranoseandfuranosederivqativeschemstr.styKNBbasicUUcommandsforatom-andbGond-typesettingloGcant.styKNBcommandsUUforprintingloGcantnumeresffmPЍ 'Thesew lesaredesignedtobGeoptionstyle lesusedwithinL5ffA͉TU>'ExX.ThecompletelistoftheXMTU>'EX'commandsUUisshowninAppGendixA.%'2.2" GeneralffConventions5'5N cmbx122.2.1&gUserCommandsforSp`eci edUseandforGeneralUse,n'XMTU>'ExX usercommandsareclassi edintotwotypGes,i.e.,commands forspeci eduseandthosefor'generalUUuse. 'SpGeci ed{usercommandsofXMTU>'ExXareusedtodrawanarrowrangeofstructures.k:Moreprecisely'spGeaking,theyiareshort-cutcommandsofgeneralusercommandswithaspeci cbondpatternfordrawing'carbGocyclesgorwithaspGeci cpatternofskeletalhetero-atomsfordrawingheteroGcycles.Theytakesuch'generalUUformsasfollows:KF9 ȠObM'10BFUJIT*AUUShinsaku:qXMTU>'ExX'fe>|2d^\Sformb[OPT]{SUBSLIST}forUUdrawingcarbGocycles ^\Sformd[BONDLIST]{SUBSLIST}forUUdrawingheteroGcycles:'where\Sformband\SformdmaybGeapproriatecommandnames.;oTheseareselectedfromchemical 'names}thatrepresentthecompGound-groupnamestobetypeset.@InaccordwithL5ffA͉TU>'ExXconventions,an'argumentUUinbracketsisanoption. 'TheDcommand\SformbtypGesetsacarbocycliccompoundwithaspeci cbondpatternwhichmaybGe'alteredbytheoptionalargumentOPT.Thecommand\SformdprintsaheteroGcycliccompoundwitha'spGeci cUUatompatternonitsskeleton.^1 'F*orexample, \bzdrv[OPT]{SUBSLIST}isacommandforthespGeci eduseofdrawingbenzenederivqa-'tives,Rwherethestem`\bzdrwithoutasux`v'isanabbreviationof`bGenzenederivqative'.>Thecommand'pyridinev[BONDLIST]{SUBSLIST}isacommandfordrawingpyridinederivqatives, inwhichthenitrogen'atomUUonthepyridineringisautomaticallytypGeset. 'OnAtheotherhand,EmoreelabGoratecommandsforgeneralusecanbeusedwithinXMTU>'ExX.kRTheyare'designed'ExXaresuxedwith`v',(f`vi',`h`0and`hi'.lWThesux`v'meansthatthe'commandprintsastructuralformulaofverticalform. PThesux`h'meansthatthecommandtypGesets'aostructuralformulaofhorizontalform.WhenalternativeorientationsarepGossible,v@XMTU>'ExXcommands'areUUdi erentiatedbyanadditionalsux`i'. 'TheMspGeci cationofeachargumentinaXMTU>'ExXcommandisbasedonlist-treatingmacros[6].o@Thus,'itemsUUtobGespeci edarelistedsequentiallywithorwithoutappropriatedelimeters. 'TheqargumentSUBSLISTplistssubstituentswithbGonds.Theargument !", cmsy10f1==Cl;3D==O;::: g,for'example,-meansthatpGosition1takesachlorineatom(Cl)throughasinglebGond,-position3takesan'oxygen]atom(O)+throughadoublebGond,Gandsoon.Thus,GacharacterstringbGeforeeverysemicolon'representsNamoGdeofsubstitution, wherealocantnumbGerwithabondmodi erisseparatedfroma'substituenttbymeansofadoubleequalitysymbGol(==).NEachbGondmodi erconsistsofoneortwo'charactersYlistedinT*able2.2.FThediagramsbGelowT*able2.2illustratethesebGondmodi ersbyusinga'cyclohexaneUUskeleton(\cyclohexanev). 'ThetoptionalargumentOPTLof\Sformbcontainsastringofoneortwocharactersforgivingapattern'of;doublebGonds(e.g.,@`r'foraright-handsetofaromaticdoublebonds`l'foraleft-handsetofaromatic'doublebGonds,and`c'foranaromaticcircleforthemacro\bzdrv).7SincetheargumentOPTisanoption,'aUUdefaultsetofbGondsisusedwhenomitted. 'The}optionalargumentBONDLIST^containsacharacterstring,Geachcharacterofwhichisusedfor'assigningaspGeci cinnerdoublebond(e.g.,`a',`b',:::Mforthedoublebondsofagivenbond-numbering).'JffH J= "5-:1LIfIwÎetakeastrictlysystematicapproach,FtheK cmsy8nZCscmtt8ZSformdshouldb'ExX11'fe>|2|ySJT*ableUU2.2:qLoGcantnumbGeringandbondmodi ersforSUBSLISTF `$L͉ffwäfdBondUUMoGdi ers8PrintedUUstructuresffwánDU*exoGcyclicUUdoublebondatn-atom nUUornSU*exoGcyclicUUsinglebondatn-atomnAU*alphaUUsinglebGondatn-atomnBU*bGetaUUsinglebondatn-atomnSAU*alphaUUsinglebGondatn-atom(dottedline)nSBU*bGetaUUsinglebondatn-atom(boldface)nSaU*alphaUU(notspGeci ed)singlebondatn-atomnSbU*bGetaUU(notspeci ed)singlebondatn-atomffwÎop8edO line10"hVZɧ"yp8edbɧbop8bhVZbyp8""VݲPfeh#(ݲPfevV1y=ed8feJòB2ɲZ"F'"J޲3㲪bFbvV4y=؄8feVV%5^VZ㲪"\V*"VV%òB6^VZɲZb\V*'bϟed"Ϭɧ"ϟedbୟɧbϟbϬbϟ"ୟ"{ݲPfeyݲPfeݭ)1A`iʄ̎`i„̎`i˺̎`i˲̎`i˪̎`iˢ̎`i˚̎`i˒̎òB2AzG̎1)l̎ ̎Ą̎Uϟp̎ ̎ÓȄ̎zut̎3AzG̎1) d̎ '̎/ ̎Uϟ6`̎ =̎ÓE̎zuL\̎ݭ)4A`if̎`if̎`if̎`if̎`if&̎`if.̎`if6̎`if>̎,5AF̎͆z̎}̎vN̎FoᲸ̎Ɔh"̎a̎Ze̎FSL`̎,òB6AF̎͆2V̎}K̎ve̎Fo̎ƆhŘ̎aIJD̎Zڄ̎FSp̎>fed"7ɧ"HfedbO7Dɧb>fb7bHf"O7D"YݲPfe6VݲPfeE1BGed8̎f7xòB2BY7DɲZO linew10"[7t'"f7x޲3BY7D㲪b[7tbE4BG؄8̎5B-㲪"+X"òB6B-ɲZb+X'buuGed"ɧ"edb5aɧbbb"5a"/ݲPfesݲPfe5-1SaedNӟedʟ1SbedT3edTϟ02Sa5a匄fd8跟2Sb5aɲZhDzZϟ3Sa5a܄fd8跟3Sb5a粪Th鲪T5-4SaTNӟTʟ4Sb3r+5Sam܄fd8y1ڟ5Sb粪U鲪r+06Sam匄fd8y1ڟ6SbɲZTUDzZTred" X>ɧ"redb%ɧbrb X>br"%"/XȟݲPfe % ݲPfe"Ɵ1SA ʄ̎ ̎ ^^̎!!$̎")B̎#0Z9`̎$7~̎%?˜̎F1SBredT>̟edT>?h02SA/%̎1%̎3%̎5%̎7%̎9%̎;%ğ̎=%̟̎8?P2SB/ɲZ0JDzZ>?h3SA/%̎1%̎3%̎5%̎7%̎9%̎;%ğ̎=%̟̎8?P3SB/粪T0J鲪T"Ɵ4SA f̎ ̎ ^ʄ̎!!튬̎")A̎#0Zp̎$7R̎%?f4̎F4SBr>̟ğ5SA ؟̎ П̎ȟ̎̎̎̎̎̎V5SBX>粪$鲪ğ06SA ؟̎ П̎ȟ̎̎̎̎̎̎V6SBX>ɲZT$DzZT ܠObM'12BFUJIT*AUUShinsaku:qXMTU>'ExX'fe>|2 'SinceХtheargumentBONDLISTЅisanoption,yadefaultisusedwhenomitted:hgthecommands\Sformd 'and$\Sformc(fordrawingheteroGcycles)typGesetdefaultsetsofbonds,.whilemostSformacommands(for'drawingUUcarbGocycles)printfullysaturatedskeletons. 'The?argumentA*TOMLIST+(e.g.,9f1==O;4==Og)containsheteroatomsandtheirpGositionsonthe'ringistructuretobGeprinted:1thisexampleargumentproGducesadioxaneskeleton,whenusedincommand'\sixheterov. ObM2 'UChapter 32'TSix-Mem8b ered T{Carbocycles:'3.1" DrawingffBenzeneDerivatives'3.1.1&gVerticalFormsofBenzeneDeriv@ativesuT'Themacro\bzdrvisusedtodrawbGenzenederivqativesofverticaltypGe(carom.sty).9Theformatofthis 'commandUUisasfollows: \bzdrv[OPT]{SUBSLIST}'TheΔnameandargumentsofthiscommandconformtothegeneralconventionsdescribGedinthepreceding'chapter.a4LoGcant#numbers#fordesignatingsubstitutionpositionsintheSUBSLIST#arerepresentedbythe'followingUUdiagram:b/A6< lcircle10tA֟dA֟ed"'ɧ"A֟edb[ɧbA֟b'bA֟"["(ݲPfeƟݲPfeۨfe:\bn=b:ɘ"n("(01(lr)ed8fe[òB2(r)[ɲZ"['"[޲3(r)[㲪b[b(04(lr)؄8fe5(l)'㲪"'ȟ"òB6(l)'ɲZb'ȟ'b͟ff?ff:q(400,240):q(0,0)>τffffff?5'inwhichacharactersetinparenthesesrepresentthehandednessofeachpGosition.mInaccordwiththe'defaultLde nitonsofthemacrobzdrv,eachoftheright-handedpGositions(2and3)isdesignedtotakeonly'aCright-handedsubstituent, whileeachoftheleft-handedpGositions(5and6)istotakeonlyaleft-handed'substituent.mSuchpGositions(designatedwiththeletter`r'or`l')arereferredtoas`oriented'positions'in|thismanual.=Incontrast,Fthetop(andalsothebGottom)positionofabenzenering(designatedwith'theistring`lr')canaccommoGdateasubstituentofbothhandedness.hItisreferredtoasa`double-sided''pGositioninthismanual. Althoughthedefaultde nitionistoputaright-handedmoiety*,aleft-handed'substituentUUcanbGeprintedbymeansofthemacro\lmoiety. 'ThesymbGolsandinthediagramrespectivelyrepresentthereferencepGointandtheinneroriginof'theUUmacro.qThesewillbGedescribedindetailinChapter14. 'Thet+optionalargumentOPTsspGecifyingabondpatternareshowninT*able3.1.IThereby*,awide'vqarietyofbGondpatterns(suchastwopatternsofbGenzenedoublebondsaswellasanaromaticcircle)can'bGeUUdepicted. 'TheV!argumentSUBSLISTUisusedtospGecifyeachsubstituentwithaloGcantnumbGerandabondmodi er'shownUUinT*able2.2,inwhichnisanarabicnumeralbGetween1and6.qF*orexample,thestatements,'\bzdrv{1==Cl;2==F}Kβ13ObM'14BFUJIT*AUUShinsaku:qXMTU>'ExX'fe>|2U JTbT*ableUU3.1:qArgumentOPTforcommandsn?bzdrvandnbzdrh^IXgff.{fdCharacterYgPrintedUUstructureff.{noneUUorr=cright-handedUUsetofdoublebGonds l=cleft-handedUUsetofdoublebGondsc=caromaticUUcircleff.{fdpUUorpa=cp-bGenzoquinoneUU(A)(Oxygenatomesat1,4-pGositions)pb=cp-bGenzoquinoneUU(B)(Oxygenatomesat2,5-pGositions)pGc=cp-bGenzoquinoneUU(C)(Oxygenatomesat3,6-pGositions)ff.{fdoUUoroa=co-bGenzoquinoneUU(A)(Oxygenatomesat1,2-pGositions)ob=co-bGenzoquinoneUU(B)(Oxygenatomesat2,3-pGositions)oGc=co-bGenzoquinoneUU(C)(Oxygenatomesat3,4-pGositions)oGd=co-bGenzoquinoneUU(D)(Oxygenatomesat4,5-pGositions)oGe=co-bGenzoquinoneUU(E)(Oxygenatomesat5,6-pGositions)of=co-bGenzoquinoneUU(F)(Oxygenatomesat1,6-pGositions)ff.{.'\bzdrv[c]{1==Cl;4==F;2==CH$_{3}$}\qquad '\bzdrv[pa]{1D==O;4D==O;6==H$_{3}$C}'\bzdrv[oa]{1D==O;2D==N--SO$_{2}$CH$_{3}$;4==OCH$_{3}$;5==H$_{3}$C}.'proGduceUUthefollowingstructures:aUQoed"JUɧ"[oedbbwɧbQobJUb[o"bw"lVEݲPfeJ"ݲPfei kfeP\bN<1=bPɘ"N<1("XU󟯱Cl[|2 'proGduceUUthefollowingstructures.bPҍed"ɧ"edb5aɧbbb"5a"/ݲPfesݲPfeUfeMfeݟOed8feed8feɟCH3|sO35-OCH3TNӟT5òBNH{SO2|sCH35aɲZ"5'"red" X>ɧ"redb%ɧbrb X>br"%"/XȟݲPfe % ݲPfe, feqfeBbCH3|sOredT>̟edT"ƟOCH3redledBbCH3|sOr>̟"ƟOCH3rTlTD'3.1.2&gHorizontalFormsofBenzeneDeriv@ativesuT'Y*ouT>TH346(lr)~>.>ݟff?ff:q(240,400):q(0,0)>τffffff?5؍'F*orUUexample,thediagrams:$`hk$`Th(UT``ThjkT``hj(UhfdPhLpfdPefdfdhҟO`eʄfd8`Zfd8SCH3|sSO2{Neʄfd8Zfd8hBCH3hj催q۟`џkq۟`Tџ(UT' `T"!kT' `"!(UџfdPџLpfdPXuefdXufdKOqeʄfd8qZfd8<N{SO2|sCH3- eʄfd8- Zfd8BCH3џ催TT]'areUUtypGesetbyinputtingthestatements:'\bzdrh[pa]{4D==O;1D==CH$_{3}$SO$_{2}$--N;3==CH$_{3}$}?\qquad'\bzdrh[pa]{1D==O;4D==N--SO$_{2}$CH$_{3}$;2==CH$_{3}$} 'ItFshouldbGenotedthethecommands\bzdrvand\bzdrharebasedrespectivelyonthecommands'\cyclohexanevEfand\cyclohexanehthatwillbGedescribedinthenextsection.lwHence,Hstructuresdrawn'withUUtheformersetofcommandscanbGealsodrawnwiththelattersetofcommands. ҍ'3.2" DrawingffCyclohexaneDerivatives'3.2.1&gVerticalFormsofCyclohexaneDeriv@ativesuT'TheAmacro\cyclohexanevisusedtodrawcyclohexanederivqativesofverticaltypGe(carom.sty).7)The'formatUUofthiscommandisasfollows: \cyclohexanev[BONDLIST]{SUBSLIST}ObM'16CFUJIT*AUUShinsaku:XMTU>'ExX'fe>|2 'LoGcantɶnumbersɶ(1{6)fordesignatingsubstitutionpositionsandcharacters(a{f)forshowingbGondsto 'bGeUUdoubledarerepresentedbythefollowingdiagram:`3A6tA֟dA֟ed"'ɧ"A֟edb[ɧbA֟b'bA֟"["(ݲPfeƟݲPfec⟯1Sb(l)A֟edTedT[1Sb(r)A֟edu&ed 2Sb(r)[ɲZǏDzZ"02Sa(r)[匄fd8 3Sb(r)[粪TǏ鲪T"3Sa(r)[܄fd8c4Sb(l)A֟[4Sa(r)A֟Tu&T5Sb(l)'粪鲪zC5Sa(l)'܄fd86Sb(l)'ɲZTDzZTzC06Sa(l)'匄fd8Aҟ1E82Et3Aҟ4At5A86AaB&XbAc3xfϿXexd͟ff?ff:q(400,240):q(0,0)>τffffff?'EachcharactersetinparenthesesrepresentsthehandednessofthecorrespGondingposition, whichis xed'inUUthistypGeofmacros. 'The=optionargumentBONDLIST=yisancharacterstringinapairofbrackets,uwhereeachcharacterindi-'catesthepresenceofadoublebGondattheedgecorrespondingtothecharacter.56Thebond-correspondence'isVratherarbitraryinsomecasesbutconformstochemicalconventionsasfaithfullyaspGossibleifsuch'conventionsUUarepresence(T*able3.2).Sv{L΍%T*ableUU3.2:qArgumentBONDLISTforcommandsncyclohexanevandncyclohexanehFML͉ffԤfdCharacter=cPrintedUUstructureffԡnone=ccyclohexane a=c1,2-doubleUUbGondb=c2,3-doubleUUbGondc=c4,3-doubleUUbGondd=c4,5-doubleUUbGonde=c5,6-doubleUUbGondf=c6,1-doubleUUbGondA=caromaticUUcircleffԎ D 'TheargumentSUBSLISTforthismacrotakesageneralformat,pinwhichthemoGdi erslistedinT*able'2.2UUareused.qSuppGoseyouinputthecommands:@'\cyclohexanev{2D==O;1Sb==H$_{3}$C;1Sa==CH$_{3}$;%'3Sb==CH$_{3}$;3Sa==CH$_{3}$}?\qquad\qquad'\cyclohexanev[b]{1D==O;5Sb==CH$_{3}$;5Sa==CH$_{3}$}'The rstexampleillustratesthecasethat\cyclohexanevaccompaniesnooptionalargument.Onthe'otherʸhand,thesecondonetake[b]asanoptionalBONDLIST,whichprintsaninnerbGondbetweenʸ2'andUU3pGositions.qThus,youcanobtainthefollowingdiagrams:f$ed"ɧ"edb5aɧbbb"5a"/ݲPfesݲPfe5òBO蓟$"ß"/˘"_e"矯H3|sCedT3edT5-CH3edNӟed跟CH35a粪Th鲪TϟCH35a܄fd8red" X>ɧ"redb%ɧbrb X>br"%"/XȟݲPfe % ݲPfe, feXvO ed8fer"ed8feoCH3X>粪$鲪ꢨCH3X܄fd8 'Sinceethemacro\cyclohexanevisthebasisofthemacro\bzdrv,istructuralformulasdepictedwith'the]lattercommandcanalsobGewrittenbytheformerone..F*orexample,thequinoneacetalsdescribed'abGoveUUarealsotypesetbythefollowingstatements.àObM'CHAPTERUU3.SIX-MEMBEREDCARBOCYCLESE|17'fe>|2 '\cyclohexanev[be]{1D==O;4Sb==CH$_{3}$O;4Sa==OCH$_{3}$;2==NH--SO$_{2}$CH$_{3}$} '\qquad?\qquad'\cyclohexanev[be]{1Sb==CH$_{3}$O;1Sa==OCH$_{3}$;4Sb==CH$_{3}$O;4Sa==OCH$_{3}$}7M'These{commandsarecompletelyequivqalenttothosedescribGeabove{andproducethefollowingstructures.b*ted"ɧ"edb5aɧbbb"5a"/ݲPfesݲPfeUfeMfeݟOed8feed8feɟCH3|sO35-OCH3TNӟT5òBNH{SO2|sCH35aɲZ"5'"red" X>ɧ"redb%ɧbrb X>br"%"/XȟݲPfe % ݲPfe, feqfeBbCH3|sOredT>̟edT"ƟOCH3redledBbCH3|sOr>̟"ƟOCH3rTlT 'F*orUUthepurpGoseofdepictingthestereochemistyUUofacyclohexanering,inputthefollowing:'\cyclohexanev{2B==CH$_{3}$;3B==CH$_{3}$}\qquad\qquad '\cyclohexanev{2B==CH$_{3}$;3A==CH$_{3}$}'Thereby*,UUyoucanobtain:-ed"Oɧ"-edb ɧb-bOb-" "ٟݲPfeyݲPfe?òBCH3 ɲZ";'"?޲CH3 㲪b;bqed" ɧ"qedb#Oɧbqb bq"#O"-ݲPfe zaݲPfe:ჟòBCH3-OɲZ"/'":ჟ޲CH3-z̎/1˟ d̎0譟'̎2/ ̎4Vq6`̎6 S=̎75E̎9{L\̎'3.2.2&gHorizontalFormsofCyclohexaneDeriv@ativesuT'Thelmacro\cyclohexanehisusedtodrawcyclohexanederivqativesofhorizontaltypGe(carom.sty). The 'formatUUofthiscommandisasfollows: \cyclohexaneh[BONDLIST]{SUBSLIST}'LoGcantUUnumbersUUfordesignatingsubstitutionpositionsarerepresentedbythefollowingdiagram:A6tA`dA`kA`T(UTҟ`TÎܟkTҟ`Îܟ(UfdPLpfdPzt1Sb(l)A`bAf-bzt1Sb(l)A`"Af2"}@2Sb(l)催b\ŲObHB2Sa(lr)[Z傄8feя3Sb(r)Îܟ催"ŏ ŲO"ԟB3Sa(lr)[傄8feݏD4Sb(r)ҟ`"-"ݏD4Sa(r)ҟ`b2bяr5Sb(r)Îܟ>bŏ LqbԞ345Sa(lr)[v8fe}@r6Sb(l)>"\Lq"H346Sa(lr)[Zv8feAh1AŸ82E83Eh4AŸ6E5A@aAޟ bB.@cB.dAޟe3`f͟ff?ff:q(240,400) :q(0,0)>τffffff?z'EachcharactersetinparenthesesrepresentsthehandednessofthecorrespGondingposition, whichis xed 'inBthistypGeofmacros.:TheSUBSLISTBandtheBONDLISTformatareshowninT*able2.2and3.2,'respGectively*.'Example:7M'\cyclohexaneh{3D==O;5D==O;1Sb==CH$_{3}$;1Sa==CH$_{3}$;%'4==CH$_{2}$CO$_{2}$H}\qquad\qquad'\cyclohexaneh{4D==CH$_{2}$;3SB==CH$_{3}$;3SA==H}.ObM'18BFUJIT*AUUShinsaku:qXMTU>'ExX'fe>|2 'TheseUUcommandsproGduce:Z͟`ßk͟`Tß(UT` `TkT` `(UßfdPßLpfdP+BOI2P2P,Ƙ_Ę+34OIpTpT,f T_f TiCH3͟`bŝ-biCH3͟`"ŝ2"{CH2|sCO2H` 2fd8 1`'k 1`T'(UT/am`T+wkT/am`+w(U'fdP'LpfdPEߟCH25ameʄfd85amZfd89CH3+w傭"-ŲO")oBH*K̎*K̎*K؄̎*KЄ̎*KȄ̎*K̎*K̎*K̎>ObM2'UChapter 44'TCarb ocycles T{withFused'Six-Mem8b ered T{Rings<'4.1" DrawingffNaphthaleneDerivativesĘ'4.1.1&gVerticalFormsofNaphthaleneDeriv@ativesRэ'Themacro\naphdrvisusedtodrawnaphthalenederivqativesofverticaltypGe(carom.sty)aswellas 'vqariousUUnaphthoGquinonederivatives.qTheformatofthiscommandisasfollows:N \naphdrv[OPT]{SUBSLIST};'LoGcantUUnumbersUUfordesignatingsubstitutionpositionsarerepresentedbythefollowingdiagram:kA؍y@tAdAed"'ɧ"Aedb[dɧbAb'bA"[d"(2ݲPfevݲPfeuBed"[dɧ"uBedbʏ ɧbuBb[dbuB"ʏ "[ݲPfeޟɘbƨ(bޟ\"ƨ="\b=bɘ"("Xfe[1(lr)Bed8feTòB2(r)ԏ ɲZ"֏P'"T޲3(r)ԏ 㲪b֏Pb[4(lr)B؄8fe'5(lr)T؄8fes86(l)'㲪"'x"s8òB7(l)'ɲZb'x'b'8(lr)Ted8feff?ff:q(400,240):q(0,0)>τffffff?"2'TheoKhandednessforeachorientedordouble-sidedpGositionisshownwithacharactersetinparentheses.'TheoptionalargumentOPTisusedtospGecifyabondpatternasshowninT*able4.1.Theargument'SUBSLISTisusedtospGecifyeachsubstituentwithaloGcantnumbGerandabondmodi ershowninT*able'2.2,UUinwhichnisanarabicnumeralbGetween1and8.;'Example:'\naphdrv{1==CH$_{2}$CH=CH$_{2}$;2==OH}?\qquad'\naphdrv{6==H$_{3}$C;2==COCH$_{2}$CH$_{2}$COOH}?\hskip1.5cm'\naphdrv[o]{1Sb==Cl;1Sa==Cl;2D==O};'TheseUUcommandsproGduce:K19C8ObM'20BFUJIT*AUUShinsaku:qXMTU>'ExX'fe>|2yQ֍jOJeT*ableUU4.1:qArgumentOPTforcommandsnnaphdrvandnnaphdrhˍV$`ffCfdCharacterPrintedUUstructureffCnone=cnaphthalene A=caromaticUUcircleffCpUUorpa=c1,4-quinoneUU(A)leftaromatic,rightquinone pb=c1,4-quinoneUU(B)rightaromatic,leftquinoneffCoUUoroa=co-quinoneUU(A)(Oxygenatomesat1,2-pGositions) ob=co-quinoneUU(B)(Oxygenatomesat2,3-pGositions)oGc=co-quinoneUU(C)(Oxygenatomesat3,4-pGositions)oGd=co-quinoneUU(D)(Oxygenatomesat4,5-pGositions)oGe=co-quinoneUU(E)(Oxygenatomesat5,6-pGositions)of=co-quinoneUU(F)(Oxygenatomesat1,6-pGositions)ffCfdqUUorqa=c2,6-quinoneUU(A)qb=c2,6-quinoneUU(B)(actually3,7-pGositons)qc=c1,5-quinoneUU(C)qd=c1,5-quinoneUU(D)(actually4,8-pGositions)qe=c1,7-quinoneUU(E)qf=c1,7-quinoneUU(F)(actually2,8-pGositions)qg=c1,7-quinoneUU(G)(actually4,6-pGositions)qh=c1,7-quinoneUU(H)(actually3,5-pGositions)ffCfdPUUorPa=c:q1,4,5,8-quinoneUU(A)Pb=c1,2,5,8-quinoneUU(B)ffCfdQ=c1,2,3,4-quinoneffCOUUorOa=c1,2,5,6-quinoneUU(A) Ob=c1,2,7,8-quinoneUU(B)Oc=c1,2,3,5-quinoneUU(C)Od=c1,2,3,7-quinoneUU(D)ffCL=ObM'CHAPTERUU4.CARBOCYCLESWITHFUSEDSIX-MEMBEREDRINGSnU21'fe>|2 u(\ed" ~ɧ"2\edb92:ɧb(\b ~b2\"92:"BݲPfe LݲPfeJLed"C2:ɧ"TLedb[eɧbJLbC2:bTL"[e"e2ğݲPfeT崟ɘbW(bT崟\"W="'~\b$=b'~ɘ"$("?.feQ2rCH2|sCH=CH2T柿ed8ferf*òBOHeeɲZ"gf&'"oed"Uɧ"oedbȉqɧbobUbo"ȉq"V?ݲPfe"ݲPfe٣Oed"҉qɧ"Oedb-ɧb٣Ob҉qbO"-"ݲPfe<ɘbַ(b<\"ַ="\b<+=bɘ"<+(" efe )޲H3|sCU㲪"U"aòBCOCH2|sCH2COOH-ɲZ"]'"]ted"VZşɧ"gtedbnɧb]tbVZşbgt"n"x[OݲPfeV'ݲPfe_ed"xɧ"_edb=ɧb_bxb_"=" ݲPfeA\"ǟ="\\bZA;=b\ɘ"ZA;("uufe{uCl_edTuedT Cl_edۯedqòBOuo$"u" ˘";e"u~'4.1.2&gHorizontalFormsofNaphthaleneDeriv@ativesuT'The:macro\naphdrhisusedtodrawnaphthalenederivqativesofhorizontaltypGe(carom.sty)aswellas 'vqariousUUnaphthoGquinonederivatives.qTheformatofthiscommandisasfollows:獑'\naphdrh[OPT]{SUBSLIST}'The|formatoftheargumentOPT|pisthesameasthatof\naphdrv(T*ables4.1).Theformatofthe'argumentSUBSLISTxisthesameascollectedinT*ables2.2.YTheloGcantnumbGeringandthehandedness'ofUUsubstitutionaredesignedasfollows:xA&tA`dA`|kA`T|(UTŸ`T̟kTŸ`̟(U|fdP|LpfdPAˤ|AˤT|TŸˤT̟TŸˤ̟|fdPtʟ2A2~2Tے2T~ےtʟTAT( efd؟8(l)AN2fd8ُ45(r)Ÿ2fd8Ŏ346(r)̟>T>TH347(r)~>.>؟J1(l)ANքfd8H2(r)|ƬT[,TŎ䟔3(r)̟Ƭُ4J4(r)Ÿքfd8ݟff?ff:q(240,400):q(0,0)>τffffff?'Example:'\naphdrh{4==NH$_{2}$;5==SO$_{3}$H}\qquad'\naphdrh{5==N=NC$_{6}$H$_{4}$SO$_{3}$Na;6==OH}'TheseUUcommandsproGduce:xΟ`ğkΟ`Tğ(UT` `TkT` `(UğfdPğLpfdPΟˤğΟˤTğT` ˤTT` ˤğfdP22,Ɵ2T_ڟ2T,Ɵ_ڟTThefd|SO3|sH` 2fd8|JNH2` քfd80`&k0`T&(UT%al`T!vkT%al`!v(U &fdP &LpfdP0ˤ&0ˤT&T%alˤT!vT%alˤ!v &fdPt2`2!.(2Ta<2T!.(a<tT`Tʟefd;ޟN=NC6|sH4SO3Na+al2fd8'34OH!v>T"GƟ>T '4.2" DrawingffTfetralineDerivatives'4.2.1&gVerticalFormsofTetralineDeriv@ativesuT'Themacro\tetralinevisusedtodrawtetralinederivqativesofverticaltypGe(carom.sty)aswellas'vqariousUUnaphthoGquinonederivatives.qTheformatofthiscommandisasfollows:S[ObM'22BFUJIT*AUUShinsaku:qXMTU>'ExX'fe>|2  \tetralinev[OPT]{SUBSLIST}'LoGcantUUnumbersUUfordesignatingsubstitutionpositionsarerepresentedbythefollowingdiagram:cZy@tAdAed"'ɧ"Aedb[dɧbAb'bA"[d"(2ݲPfevݲPfeuBed"[dɧ"uBedbʏ ɧbuBb[dbuB"ʏ "[ݲPfe\b=bɘ"("XfeN1Sb(l)uBedTAedTǎ쟯1Sa(r)uBedĨedBv2Sb(r)ԏ ɲZpDzZB02Sa(r)ԏ 匄fd8Bv3Sb(r)ԏ 粪Tp鲪TB3Sa(r)ԏ ܄fd8N4Sb(l)uBAǎ4Sa(r)uBTĨT؟5(lr)T؄8fes86(l)'㲪"'x"s8òB7(l)'ɲZb'x'b؟8(lr)Ted8feff?ff:q(400,240) :q(0,0)>τffffff?xӍ'TheoKhandednessforeachorientedordouble-sidedpGositionisshownwithacharactersetinparentheses. 'TheUUoptionalargumentOPTisusedtospGecifyabondpatternasshowninT*able4.2.L΍?nT*ableUU4.2:qArgumentOPTforcommandsntetralinevandntetralineh4ML͉ffԤfdCharacter=cPrintedUUstructureffԡnone=ctetralineA=caromaticUUcircleeUUorea=c1,2-doubleUUbGondeb=c2,3-doubleUUbGondec=c3,4-doubleUUbGondffԎߍ 'AjbGondjmodi erintheargumentSUBSLISTjforn=1to4canbGeoneofthebondmodi ersshown'inm*T*able2.2,whichallows z-or -orientation.EOntheotherhandabGondmodi erintheargument'SUBSLISTfor?n,E=5to8shouldbGevqacant.IfthereappearstheovercrowdingbGetween1-and8-'substituentPorbGetween4-and5-substituent,thebGondmodi er5Sbor8SbisallowedPtoavoidPsuch'overcrowding.'Example:3'\tetralinev{1Sb==H$_{3}$C;1Sa==CH$_{3}$;%'4Sb==H$_{3}$C;4Sa==CH$_{3}$;7==Br}\qquad'\tetralinev[ea]{1==CH$_{2}$OSi(CH$_{3}$)$_{2}$C(CH$_{3}$)$_{3}$;'2==C$_{2}$H$_{5}$;5==OCH$_{3}$;6==O=CH}\qquad'\tetralinev{3D==NOH;4Sb==H$_{3}$C;4Sa==CH$_{3}$;5Sb==Cl}'TheseUUcommandsproGduce:cZ5ed".ɧ"?edbF3џɧb5b.b?"F3џ"PݲPfe-ݲPfeWMed"P3џɧ"aMedbhgɧbWMbP3џbaM"hg"r4[ݲPfe4W\b1拟=b4Wɘ"1拟("LşfeIH3|sC[MedTZ_edTegYCH3aMedbedIH3|sC[MZ_egYCH3aMTbTߟòBBr$ɲZb!'bq*ed"WLɧ"q*edbՋɧbq*bWLbq*"Ջ"W֟ݲPfe$ݲPfeed"ߋɧ"edbğɧbbߋb"ğ"ݲPfe>ɘbN(b׎\b=Ÿ=b׎ɘ"=Ÿ(" fe@CH2|sOSi(CH3)2C(CH3)3qed8feòBC2|sH5ğɲZ"'"WOCH3=؄8fe޲O=CHWL㲪"W"Ps ed"IY.ɧ"Zs edbaɧbPs bIY.bZs "a"kYݲPfeI%ݲPferȟed"kɧ"|ȟedbɧbrȟbkb|ȟ""tݲPfeOp\bM?=bOpɘ"M?("h ޟfeڟ޲NOHs؟ebtb tb  be>,H3|sCvȟusxrCH3|ȟT}TL?ǟClTs S?R'4.2.2&gHorizontalFormsofTetralineDeriv@atives'TheUU\tetralinehisthehorizontalcounterpartofthecommand\tetralinev:f&ObM'CHAPTERUU4.CARBOCYCLESWITHFUSEDSIX-MEMBEREDRINGSm23'fe>|2  \tetralineh[OPT]{SUBSLIST}tt'LoGcantUUnumbersUUfordesignatingsubstitutionpositionsarerepresentedbythefollowingdiagram:9A&tA`dA`|kA`T|(UTŸ`T̟kTŸ`̟(U|fdP|LpfdPAˤ|AˤT|TŸˤT̟TŸˤ̟|fdP~ےtʟTAT( efd؟8(l)AN2fd8ُ45(r)Ÿ2fd8Ŏ346(r)̟>T>TH347(lr)~>.>vd`1Sb(l)AˤbAVqbwq̲1Sa(l)Aˤ"AV"}0D2Sb(l)|ƬbL~b82Sa(lr)[JƄ8fe͏D3Sb(r)̟Ƭ"~"ğ3Sa(r)[Ƅ8feُ4`4Sb(r)Ÿˤ"򟴘q"ُ4̲4Sa(r)Ÿˤbbݟff?ff:q(240,400) :q(0,0)>τffffff?!L'TheoKhandednessforeachorientedordouble-sidedpGositionisshownwithacharactersetinparentheses. 'TheoptionalargumentOPTisusedtospGecifyabondpatternasshowninT*able4.2.Theargument'SUBSLISTUUisthesameasthatof\tetralinev.tt'Example:E'\tetralineh[eb]{1D==O;4D==O;5==OH}?\qquad'\tetralineh[eb]{1SB==H$_{3}$C;1SA==H;4SB==CH$_{3}$;4SA==H}'TheseUUcommandsproGduce:9$`hk$`Th(UT``ThjkT``hj(UhfdPhLpfdP$ˤh$ˤThT`ˤThjT`ˤhjhfdP1҄fd0NhTTTefdhҟOH`2fd8}JO쟷2fd8쟴˞fd8hҟJO`2fd8`˞fd8q۟`џkq۟`Tџ(UT' `T"!kT' `"!(UџfdPџLpfdPq۟ˤџq۟ˤTџT' ˤT"!T' ˤ"!џfdPXu1҄fd"ӟ! T r TXuefd`H3|sCq۟ˤbqqb>h̲H u2 ̎T9^̎@̎ϟH̎/ퟺOZ̎y V̎)^̎ GeV̎<`CH3- ˤ"/ Gq"<̲H,2 ̎.\9^̎0u@̎1WH̎39OZ̎58V̎6^̎8ߟeV̎*i'4.3" DrawingffDecalineDerivativesIi'4.3.1&gVerticalFormsofDecalineDeriv@ativesע'The)macro\decalinevisusedtodrawdecalinederivqativesofverticaltypGe(carom.sty).DTheformatof'thisUUcommandisasfollows:E \decalinev[BONDLIST]{SUBSLIST}'LoGcant&numbers&fordesignatingsubstitutionpositionsandcharactersforshowingbGondstobedoubled'areUUrepresentedbythefollowingdiagram:y,ObM'24BFUJIT*AUUShinsaku:qXMTU>'ExX'fe>|2 yA tAdAed"'ϟɧ"Aedb[ɧbAb'ϟbA"["(YݲPfeݲPfeuied"[ɧ"uiedbʏGɧbuib[bui"ʏG"\ݲPfeB$1uiedTBedTǏ1Sa(r)uiedĨedB2Sb(r)ԏGɲZ—DzZB02Sa(r)ԏG匄fd8B3Sb(r)ԏG粪T—鲪TB3Sa(r)ԏG܄fd8B$4uiBǏ4Sa(r)uiTĨTc5Sb(l)A][W5ATtTlɟ6Sb(l)'ϟ粪鲪f6Sa(l)'܄fd8lɟ7Sb(l)'ϟɲZTDzZTf07Sa(l)'匄fd8c8Sb(l)AedT]edT[W8AedtedA培0F(YɲZ8feA0G(Y8feNSa(r)ǟSb(l)N (Sa(r)ǟ (Sb(l)AџiAXkAџehYXgfuauXbuc_j]dff?ff:q(400,240) :q(0,0)>τffffff? 'TheoKhandednessforeachorientedordouble-sidedpGositionisshownwithacharactersetinparentheses. 'TheWoptionargumentBONDLISTisbasedontheassignmentofcharacters(a{k)torespGectivebGondsas'shownintheabGovediagram./AbGondmodi erintheargumentSUBSLISTfornŲ=1{8canbeoneof'bGondNmodi ersshowninT*able2.2.oThesubstitutionatthebridgeheadpositionsisdesignatedasshown'inUUT*able4.3.L΍3xT*ableUU4.3:qSUBSLISTforbridgeheadpGositionsinndecalinevandndecalineh:oL͉ff*fdCharacterW PrintedUUstructureff*0FA=calphaUUsinglebGondat8a 0FB=cbGetaUUsinglebondat8a0FU=cunspGeci edUUsinglebondat8a0GA=calphaUUsinglebGondat4a0GB=cbGetaUUsinglebondat4a0GU=cunspGeci edUUsinglebondat4aff*5'Example:č'\decalinev{1D==O;0FB==H;0GA==H}?\qquad'\decalinev{1B==CH$_{2}$OSiR$_{3}$;3D==O;4A==COOCH$_{3}$;%'0FB==CH$_{3}$;0GA==H}Ӎ'TheseUUcommandsproGduce:c덍{ed"tɧ"edb4Ÿɧb{btb"4Ÿ"ݲPfesԟݲPfeNed"4Ÿɧ"Nedbh~ɧbNb4ŸbN"h~"5LݲPfe4O6ed8feNed8feH\ɲZ8̎H\̎\̎\ ̎\(̎\0̎\8̎\@̎\H̎ red"X=ɧ"redbɧb rbX=br""%XǟݲPfe% ݲPfe,ןed"%ɧ"6ןedb=ɧb,ןb%b6ן"="GݲPfe31CH2|sOSiR36?qed8̎T޲OGrebIsbH bJ  b31COOCH36?qf̎6?qf̎6?qf̎6?qf̎6?qf&̎6?qf.̎6?qf6̎6?qf>̎"rSCH3%%ɲZ8̎"rSH%%̎%%̎%% ̎%%(̎%%0̎%%8̎%%@̎%%H̎Fٍ'4.3.2&gHorizontalFormsofDecalineDeriv@atives蛍'ThePmacro\decalineh(carom.sty)isthehorizotalcounterpartof\decalinev.aTheformatandthe'assignmentofBONDLISTnandSUBSLISToftheformermacroarethesameasthelatter(seeT*ables2.2'andUU4.3). \decalineh[BONDLIST]{SUBSLIST}Ӎ'LoGcantUUnumbersUUfordesignatingsubstitutionpositionsarerepresentedbythefollowingdiagram:ObM'CHAPTERUU4.CARBOCYCLESWITHFUSEDSIX-MEMBEREDRINGSm25'fe>|2 AtAn`dAn`dkAn`Td(UT۪`TkT۪`(UdfdPdLpfdPAnˤdAnˤTdT۪ˤTT۪ˤdfdPo8Sb(r)An`bA>-bqq8Sa(l)An`"A>2"ӏ5Sb(r)۪`"ڟ-"ӏ5Sa(r)۪`bڟ2bǎr6Sb(r)>bLqb346Sa(r)[v8fe}}r7Sb(l)d>"4Lq" 347Sa(lr)[2v8fepL`1Sb(l)AnˤbA>qbqq̲1Sa(l)Anˤ"A>"}}D2Sb(l)dƬb4~b 2Sa(lr)[2Ƅ8feǎ쟝D3Sb(r)Ƭ"䟣~"3Sa(r)[Ƅ8feӏ`4Sb(r)۪ˤ"ڟq"ӏ̲4Sa(r)۪ˤbڟbxʟ(0F(l),fd8B&(0G(r)fd8@iA kB@eBfAghn˄aAPbB˄cBdjff?ff:q(240,400) :q(0,0)>τffffff?-'TheUUhandednessforeachorientedordouble-sidedpGositionisshownwithacharactersetinparentheses.'Example:'\decalineh{1D==O;0FA==H;0GB==H}?\qquad\qquad '\decalineh{1B==R$_{3}$SiOCH$_{2}$;3D==O;4A==COOCH$_{3}$;%'0FB==CH$_{3}$;0GA==H}'TheseUUcommandsproGduce:󧍍#`hk#`Th(UT_`ThikT_`hi(UhfdPhLpfdP#ˤh#ˤThT_ˤThiT_ˤhihfdPsJO}럷2fd8}럴˞fd8}؟(HK̎K̎K̎K̎K̎K̎K̎{K̎۟(HhiK8qܟ`ҟkqܟ`Tҟ(UT1 `T,"kT1 `,"(UҟfdPҟLpfdPqܟˤҟqܟˤTҟT1 ˤT,"T1 ˤ,"ҟfdPϓJR3|sSiOCH2q2 82:O-rX.*شd, dFJCOOCH362 ̎82 ̎:Ÿ2 ̎<ʟ2 ̎>ҟ2 ̎@ڟ2 ̎B⟶2 ̎Dꟶ2 ̎:(CH3 K8'ExX'fe>|2ObM2 'UChapter 52'TFused T{TricyclicCarb ocyclesand'Steroids:'5.1" DrawingffAnthraceneDerivatives'5.1.1&gCommandforSp`eci edUseuT'Themacro\anthracenevisusedtodrawanthracenederivqativesofverticaltypGe(carom.sty)aswellas 'vqariousUUquinonederivatives.qTheformatofthiscommandisasfollows: \anthracenev[OPT]{SUBSLIST}'LoGcantUUnumbersUUfordesignatingsubstitutionpositionsarerepresentedbythefollowingdiagram:_'o@tAdAed"'ɧ"Aedb[cɧbAb'bA"[c"(1ݲPfeuݲPfeuAed"[cɧ"uAedbɧbuAb[cbuA""[ݲPfeѨed"ʏɧ"ۨedb۟ɧb쏩ݲPfeۨ"۟"ѨbʏbBɘbe(bB\"e="ݟ\bu=bݟɘ"u("\b=bɘ"("ufe'ߟ5(lr)S؄8fei76(l)|'㲪"z'w"i7òB7(l)|'ɲZbz'w'b'ߟ8(lr)Sed8fe؏W1(lr)u˟ed8feòB2(r)۟ɲZ" '"޲3(r)۟㲪b b؏W4(lr)u˟؄8fe[9(lr)Bed8fe[10(lr)B؄8feff?ff:q(400,240):q(0,0)>τffffff?-'TheoKhandednessforeachorientedordouble-sidedpGositionisshownwithacharactersetinparentheses.'TheoptionalargumentOPTisusedtospGecifyabondpatternasshowninT*able5.1.Theargument'SUBSLISTisusedtospGecifyeachsubstituentwithaloGcantnumbGerandabondmodi ershowninT*able'2.2,UUinwhichnisanarabicnumeralbGetween1and10.u'Example:'\anthracenev[pa]{9D==O;{{10}D}==O;2==COOH}\hskip1.5cm'\anthracenev[pA]{9D==O;{{10}D}==O;2==COOH}'TheseUUcommandsproGduce:_'qned"jTğɧ"{nedbɧbqnbjTğb{n""UNݲPfej!ݲPfe^ed"ɧ"^edb<ɧb^bb^"<" ݲPfeed"<ɧ"edbɧbмƟݲPfe""b<boɘb (bo\" ="p\bn;:=bpɘ"n;:("fetfe,òBCOOHɲZ"('"O;ed8feded8feO;؄8fed؄8fe]ed" ɧ"]edb%8;ɧb]b b]"%8;"/ ݲPfe MݲPfe6Red"/8;ɧ"@RedbGkɧb6Rb/8;b@R"Gk"Q8şݲPfeX՟ed"Qkɧ"b՟edbiɧbslݲPfeb՟"i"X՟bQkbVR崮+òBCOOHsɲZ"u'"=8sO>믟ed8feARed8fe=8sO>믟؄8feAR؄8feK27ObM'28BFUJIT*AUUShinsaku:qXMTU>'ExX'fe>|2apy>e T*ableUU5.1:qArgumentOPTforcommandsnanthraceneve32xR4ffϸfdCharacter]'PrintedUUstructureffϸnoneUUorr=cright-handedUUdoublebGonds l=cleft-handedUUdoublebGondsA=caromaticUUcircleffϸfdpUUorpa=c9,10-anthraquinoneUU(A)pA=c9,10-anthraquinoneUU(circletypGe)ffϸfdo=c1,2-anthraquinoneUU(A)oa=c1,2-anthraquinoneUU(A')oA=c1,2-anthraquinoneUU(circletypGe)ob=c2,3-antharquinoneUU(B)oGc=c1,2-anthraquinoneUU(C)ffϸfdq=c1,4-anthraquinoneUU(A)qa=c1,4-anthraquinoneUU(A')qA=c1,4-anthraquinoneUU(circletypGe)ffϸ<'5.1.2&gCommandforGeneralUseڍ'Themacro\hanthracenev(carom.sty)isamoregeneralmacrothananthracenev,wherethelatteris 'actuallyUUashort-cutcommandoftheformer.qTheformatofthiscommandisasfollows:y} \hanthracenev[BONDLIST]{SUBSLIST}['LoGcantnumbers(1{12)fordesignatingsubstitutionpositionsandbonddescriptors(a{p)arerepresented'byUUthefollowingdiagram:mLj@tAJPdAJe"'l"AJeb[(bAJPb'lϼbAJP"[(ϼ"'ɲZPfe:ɲZPfeue"[("ueb䟵buPb[(ϼbuP"ϼ"[ɲZPfęŸe"Ŏ䟵"֨Ÿeb bnɲZPfe֨ŸP" ϼ"̨ŸPbŎϼbwcF5Sb(l)AJP PZ5AJPTtPTaVl6Sb(l){'lӲZyղZ[uR̘6Sa(l)s'4匄fd8aV7Sb(l){'l Ty T[uR7Sa(l)s'4<fd8wcF8Sb(l)AJeT eTZ8AJete5z1ШŸeTureTl1Sa(r)֨Ÿeeu2Sb(r)  🳲 v2Sa(r) <fd8ul3Sb(r) ӲZTղZTv̘3Sa(r) 匄fd85z4ШŸPurPl4Sa(r)֨ŸPTPT9ueTAeT9ueVe10uPAP10uPTVPTA12F' 8feAಶ12G'ײ8feu>11F[ 8feu>ಶ11G[ײ8feh8Saٟ(r)d8Sbd(l)hSa(r)dSbd(l)$8SaՕ(r) 8Sb (l)$SaՕ(r) Sb (l)AnkApAnXg@j{䆟i>Xhu*muVou*XenlXfߨ柯abߨXcﶟnﶟXdYff?ff:q(400,240):q(0,0)>τffffff?3K'TheoKhandednessforeachorientedordouble-sidedpGositionisshownwithacharactersetinparentheses.'TheR`optionargumentBONDLISTR_isbasedontheassignmentofcharacters(a{p)torespGectivebGondsas'shown;intheabGovediagramandT*able5.2.^zA'bGondmodi erintheargumentSUBSLIST'fornJ=1{10'isgselectedfromthoseshowninT*able2.2.ThesubstitutionatthebridgeheadpGositionsisdesignatedas'shownUUinT*able5.3.['Example:'\hanthracenev[C]{5==\lmoiety{CH$_{3}$O};%'8==\lmoiety{CH$_{3}$O};9==CN;{{10}D}==O}\qquad'\hanthracenev[hjp]{{{11}FA}==H;{{11}GA}==H;1A==OBz;4B==OH;2D==O}['TheseUUcommandsproGduce:ObM'CHAPTERUU5.FUSEDTRICYCLICCARBOCYCLESANDSTEROIDSw<29'fe>|2ӇL΍SET*ableUU5.2:qArgumentBONDLISTforcommandsnhanthracenevJVL͉fffdCharacterHg"PrintedUUstructureff򡍍none=cpGerhydro-anthracene a=c1,2-doubleUUbGondb=c2,3-doubleUUbGondc=c3,4-doubleUUbGondd=c4,4a-doubleUUbGonde=c10,4a-doubleUUbGondf=c10,10a-doubleUUbGondg=c5,10a-doubleUUbGondh=c5,6-doubleUUbGondi=c6,7-doubleUUbGondj=c8,7-doubleUUbGondk=c8,8a-doubleUUbGondl=c9,8a-doubleUUbGondm=c9,9a-doubleUUbGondn=c1,9a-doubleUUbGondo=c4a,9a-doubleUUbGondp=c10a,8a-doubleUUbGondA=crightUUaromaticcircleB=ccentralUUaromaticcircleC=cleftUUaromaticcircleff򎎎 .)JhQ(T*ableUU5.3:qSUBSLISTforbridgeheadpGositionsinnhanthracenev^̍}1off*fdCharacterY PrintedUUstructureff*11FA=calphaUUsinglebGondat9a 11FB=cbGetaUUsinglebondat9a11FU=cunspGeci edUUsinglebondat9a11GA=calphaUUsinglebGondat4a11GB=cbGetaUUsinglebondat4a11GU=cunspGeci edUUsinglebondat4aff*fd12FA=calphaUUsinglebGondat8a12FB=cbGetaUUsinglebondat8a12FU=cunspGeci edUUsinglebondat8a12GA=calphaUUsinglebGondat10a12GB=cbGetaUUsinglebondat10a12GU=cunspGeci edUUsinglebondat10aff*ؠObM'30CFUJIT*AUUShinsaku:XMTU>'ExX'fe>|2 u|Ŏed"uɧ"Ŏedblɧb|ŎbubŎ"l":ݲPfeux~ݲPfeJed"lɧ"Jedb(ɧbJblbJ"("ݲPfe-ed"(ɧ"-edbFɧbݲPfe-"F"-b(bz\崮o⦟CH3|sO\؄8feo⦟CH3|sO\ed8feߤCNed8feߤO؄8feP؄8feped"ɧ"pedbNɧbpbbp"N"#ݲPfez`ݲPfe*,ed"#Nɧ"4,edb< ɧb*,b#Nb4,"< "E؟ݲPfeM.ed"F ɧ"W.edb^HƟɧbhݲPfeW."^HƟ"M.bF b-ԟ\b=b-ԟɘ"(" aBfeTBOBzVȂʄ̎VȂ„̎VȂ˺̎VȂ˲̎VȂ˪̎VȂˢ̎VȂ˚̎VȂ˒̎TBOHVȂ؄8̎uHòBOg$"i("h˘"jğe"BdHE̎E̎E̎E̎E̎E̎E̎E̎BdHE̎E̎E ̎E(̎E0̎E8̎E@̎EH̎!'5.2" DrawingffPhenanthreneDerivatives'5.2.1&gCommandforSp`eci edUseuT'Themacro\phenanthrenevisusedtodrawphenanthrenederivqativesofverticaltypGe(carom.sty)aswell 'asUUvqariousquinonederivatives.qTheformatofthiscommandisasfollows:# \phenanthrenev[OPT]{SUBSLIST}'LoGcantUUnumbersUUfordesignatingsubstitutionpositionsarerepresentedbythefollowingdiagram:ʍo@tAdAed"'ɧ"Aedb[cɧbAb'bA"[c"(1ݲPfeuݲPfeuAed"[cɧ"uAedbɧbuAb[cbuA""[ݲPfeBedPfe"uAZ"ʏbѨZbu˟edPfeʏɲZ"Ѩo"(fe(Kb"ھ"ɘ"("\b=bݟ\"="b[bWfe'ߟ5(lr)Sed8fei7òB6(l)|'ɲZbz'w'bi7޲7(l)|'㲪"z'w"'ߟ8(lr)S؄8fe[9(lr)B؄8fe׏S10(r)ʏ㲪b̏Ob1e1(r)ۨedbݩ-Ƙb1d2(r)ۨe"ݩ-1"uyd3(lr)[ퟡ8feџd4(l)uAebu1bff?ff:q(400,240):q(0,0)>τffffff?P'TheoKhandednessforeachorientedordouble-sidedpGositionisshownwithacharactersetinparentheses.'TheUUoptionalargumentOPTisusedtospGecifyabondpatternasshowninT*able5.4.2b_T*ableUU5.4:qArgumentOPTforcommandsnphenanthrenevS32m៺4ffݤfdCharacterRCPrintedUUstructureffݡnoneUUorr=cright-handedUUdoublebGondsA=caromaticUUcircleffݡpUUorpa=c1,4-quinoneUU(A)pA=c1,4-quinoneUU(circletypGe)ffݡoUUoroa=c1,2-quinoneUU(A)oA=c1,2-quinoneUU(circletypGe)ob=c2,3-quinoneUU(B)oGc=c3,4-anthraquinoneUU(C)ffݡqUUorqa=c9,10-quinoneqA=c9,10-quinoneUU(circletypGe)ffݎʍ 'TheuargumentSUBSLISTuisemployedtospGecifyeachsubstituentwithaloGcantnumbGerandabond'moGdi erUUshowninT*able2.2,inwhichnisseledtedtobGeanarabicnumeralbGetween1and10.ڑ'Example:φObM'CHAPTERUU5.FUSEDTRICYCLICCARBOCYCLESANDSTEROIDSw<31'fe>|2 '\phenanthrenev[q]{9D==O;{{10}D}==O;2==COOH}\hskip1.5cm '\phenanthrenev[qA]{9D==O;{{10}D}==O;2==COOH}"}'TheseUUcommandsproGduce:!qned"jTğɧ"{nedbɧbqnbjTğb{n""UNݲPfej!ݲPfe^ed"ɧ"^edb<ɧb^bb^"<" ݲPfeo,edPfe<"^Z"<bZb蟿edPfe<ɲZ"o"VfeU؟Kb" ھ"pɘ"n;:("p\bn;:=b"bԟbtfeO;؄8fed؄8fepOonebob b : bNdCOOHe"J1"]ed" ɧ"]edb%8;ɧb]b b]"%8;"/ ݲPfe MݲPfe6Red"/8;ɧ"@RedbGkɧb6Rb/8;b@R"Gk"Q8şݲPfe@矿edPfeGk"@RZ"QkbX՟ZbbRedPfeQkɲZ"X՟o"E8şn+=8sO>믟؄8feAR؄8fe^l+OQ)ebSYbQşbS bo dCOOHb՟e"d1";4'5.2.2&gCommandforGeneralUse'The<;macro\hphenantherev(carom.sty)isamoregeneralmacrothanphenanthrenev,A@wherethelatter'isUUashort-cutcommandbasedontheformer.qTheformatofthiscommandisasfollows:- \hphenanthrenev[BONDLIST]{SUBSLIST}'LoGcantnumbers(1{12)fordesignatingsubstitutionpositionsandbonddescriptors(a{p)arerepresented'byUUthefollowingdiagram:"Cj@tAJPdAJe"'l"AJeb[(bAJPb'lϼbAJP"[(ϼ"'ɲZPfe:ɲZPfeue"[("ueb䟵buPb[(ϼbuP"ϼ"[ɲZPfeAԟePfe䟓"uZ]"Ŏ䟓b̨ŸZ]buePfeŎ䟵 "̨Ÿo{"wcF5Sb(l)AJeT eTZ5AJeteaV6Sb(l){'l Ty T[uR6Sa(l)s'4<fd8aVl7Sb(l){'lӲZyղZ[uR̘7Sa(l)s'4匄fd8wcF8Sb(l)AJP PZ8AJPTtPT9uPAP9Sa(r)uPTVPTB:l10Sb(r)ŎӲZT4ղZTBR̘10Sa(r)Ŏ匄fd8\&1Sb(r)֨ŸeTeT\0K1Sa(r)֨ŸFfd8\f2Sb(r)֨ŸdĬd\02Sa(r)֨Ÿfd8}d\3Sb(l)䟍άT[Tɨ}d\3Sa(r)Ŏ䟍ά4Hf4a(l)udĬTAdTğ4tΟfd8' 8feAಶ12G'ײ8feuebt֟1bҏ²>11GŎ䟻 bǏ=bSb(r)dSbd(l)AnfApAnXj"gyh䲟Xiu*ouVmu*XlŸelXkΏzbُ4aΏnǠzcլdYff?ff:q(400,240):q(0,0)>τffffff?'TheoKhandednessforeachorientedordouble-sidedpGositionisshownwithacharactersetinparentheses,'whereUUthedesignationofovercrowdedUUpGositionsisabbreviated.  'The coptionargumentBONDLIST Visbasedontheassignmentofcharacters(a{p)torespGectivebGonds'asshownintheabGovediagramandT*able5.5.SAbGondmodi erintheargumentSUBSLISTforn=1{10'can)bGeoneofbondmodi ersshowninT*able2.2.c;Thesubstitutionatthebridgeheadpositionsissimilar'toUUthatdesignatedinT*able5.3for\hanthracenev."}'Example:-'\hphenanthrenev[acgikm]{{{11}F}=={\kern-3em\raise1ex\hbox{H}};%'{{12}F}==\lmoiety{H~~}}\hskip1.5cm'\hphenanthrenev[acoj]{7D==O;{{12}FB}==}'TheseUUcommandsproGduce: ;ObM'32BFUJIT*AUUShinsaku:qXMTU>'ExX'fe>|2=GL΍MHT*ableUU5.5:qArgumentBONDLISTforcommandsnhphenanthrenev4L͉ff#fdCharacterJ|zPrintedUUstructureff#none=cpGerhydro-phenanthrene a=c1,2-doubleUUbGondb=c2,3-doubleUUbGondc=c3,4-doubleUUbGondd=c4,4a-doubleUUbGonde=c4a,4b-doubleUUbGondf=c4b,5-doubleUUbGondg=c5,6-doubleUUbGondh=c6,7-doubleUUbGondi=c7,8-doubleUUbGondj=c8,8a-doubleUUbGondk=c8a,9-doubleUUbGondl=c9,10-doubleUUbGondm=c10,10a-doubleUUbGondn=c1,10a-doubleUUbGondo=c4a,10a-doubleUUbGondp=c4b,8a-doubleUUbGondA=crightUUaromaticcircleB=ccentralUUaromaticcircleC=cleftUUaromaticcircleff#ލqned"jTğɧ"{nedbɧbqnbjTğb{n""UNݲPfej!ݲPfe^ed"ɧ"^edb<ɧb^bb^"<" ݲPfeo,edPfe<"^Z"<bZb蟿edPfe<ɲZ"o"VfeU؟Kb" ھ"pɘ"n;:("p\bn;:=b;\b.=bodfewcHUNɲZ8fe")H^edb.21b]ed" ɧ"]edb%8;ɧb]b b]"%8;"/ ݲPfe MݲPfe6Red"/8;ɧ"@RedbGkɧb6Rb/8;b@R"Gk"Q8şݲPfe@矿edPfeGk"@RZ"QkbX՟ZbbRedPfeQkɲZ"X՟o"_ɟfeHKb"Ekǟھ"F[bD8b\"!Qş="=-޲OQMe"Q"" ".՟ɲZ8̎8b'5.3" DrawingffSteroidDerivativesG'TheKLmacro\steroid(carom.sty)typsetsasteroidderivqativewithoutthesidechain.noTheformatofthis 'commandUUisasfollows:& \steroid[BONDLIST]{SUBSLIST}!}'LoGcantCnumbersC(1{17)fordesignatingsubstitutionpositionsandbonddescriptors(a{t)arerepresented'byUUthefollowingdiagram:!ObM'CHAPTERUU5.FUSEDTRICYCLICCARBOCYCLESANDSTEROIDSy33'fe>|2. j@tAJPdAJe"'l"AJeb[(bAJPb'lϼbAJP"[(ϼ"'ɲZPfe:ɲZPfeue"[("ueb䟵buPb[(ϼbuP"ϼ"[ɲZPfeAԟePfe䟓"uZ]"Ŏ䟓b̨ŸZ]buePfeŎ䟵 "̨Ÿo{" "֨ŸZ]" b~Z]bLePfe֨ŸFfd"3wcF1Sb(l)AJeT eTZ1AJeteaV2Sb(l){'l Ty T[uR2Sa(l)s'4<fd8aVl3Sb(l){'lӲZyղZ[uR̘3Sa(l)s'4匄fd8wcF4Sb(l)AJP PZ4AJPTtPT6uPAP6Sa(r)uPTVPTB:l7Sb(r)ŎӲZT4ղZTBR̘7Sa(r)Ŏ匄fd8ɨ}d\12Ŏ䟍ά4pܠ}d\12Sb(l)䟍άT[T쟌f11Sb(l)udĬTAdTt11tΟfd8쟮K15Sa(r)~Ffd8ԟ&15Sb(r)~eTΟeT쟙16Sa(r)~fd8ԟf16Sb(r)~dĬΟdJ}d\17Sa(r) άT}d\17 άTPTAಶ5'ײ8feA10' 8feu>8[ 8fe[`ep9AԟeL8feӏep14ueL8feӏR13udĄ8feAnjAkAnXd"aybzXcu*huVgu*XfniŸXeΏznُ4oΏpydzm2 lğzs🣱rt@zt qYff?ff:q(400,240) :q(0,0)>τffffff?T'TheoKhandednessforeachorientedordouble-sidedpGositionisshownwithacharactersetinparentheses, 'whereUUthedesignationofovercrowdedUUpGositionsisabbreviated. 'The>optionargumentBONDLIST>isbasedontheassignmentofcharacters(a{t)torespGectivebGonds'asUUshownintheabGovediagramandT*able5.6.ca?L΍`#=T*ableUU5.6:qArgumentBONDLISTforcommandsnsteroiddML͉ff'UzfdCharacter?PrintedUUstructure)B ffCharacterjPrintedUUstructureff'Uznone=csteroidUUskeleton)E ff a=c1,2-doubleUUbGondϟ ffbP2,3-doubleUUbGondc=c3,4-doubleUUbGondϟ ffdP4,5-doubleUUbGonde=c6,5-doubleUUbGondϟ fffP6,7-doubleUUbGondg=c7,8-doubleUUbGondϟ ffhP9,8-doubleUUbGondi=c9,10-doubleUUbGond Ο ffjP1,10-doubleUUbGondk=c5,10-doubleUUbGond Ο fflP9,11-doubleUUbGondm=c12,11-doubleUUbGond͟ ffnP12,13-doubleUUbGondo=c14,13-doubleUUbGond͟ ffpP8,14-doubleUUbGondq=c14,15-doubleUUbGond͟ ffrP15,16-doubleUUbGonds=c17,16-doubleUUbGond͟ fftP17,13-doubleUUbGondA=caromaticUUAringLџ ffBParomaticUUBringC=caromaticUUCring ffff'UzL 'ACbGond^modi erintheargumentSUBSLISTCfornq&=1{17(exceptfusedpGositions)isselectedfrom'thelistofbGondmodi ers(T*able2.2).[NThesubstitutionatthefusedpositions(n=5,8,9,10,13and14)is'similarlyUUdesignatedasforfusedbicylicortricycliccompGounds(T*able5.7).r񚍟L΍j"T*ableUU5.7:qSUBSLISTforfusedpGositionsinnsteroid.fqkL͉ffȤfdCharacterp@ PrintedUUstructureffȡnUUornS=cexoGcyclicUUsinglebondatn-atom nA=calphaUUsinglebGondatn-atom(boldface)nB=cbGetaUUsinglebondatn-atom(dottedline)nU=cunspGeci edUUsinglebondatn-atomffȎЍ'Example:"ObM'34BFUJIT*AUUShinsaku:qXMTU>'ExX'fe>|2 '\steroid[ackhf]{{{13}B}==\lmoiety{H$_{3}$C};{{14}A}==H}\hskip1cm '\steroid[d]{3D==O;9A==Br;{{11}D}==O;%'{{17}B}==COCH$_3$;{{14}A}==H;%'{{13}B}==\lmoiety{H$_3$C};{{10}B}==\lmoiety{H$_3$C}}C'TheseUUcommandsproGduce:~xed"qqɧ"edbzɧbxbqqb"z"rHݲPfeq>ݲPfeXed"zɧ"Xedb6ɧbXbzbX"6"ݲPfe&edPfe6"XZ"6bZbƿ⟿edPfe6ɲZ"o" "Z" b&ПZb󞟿edPfefd"3wɘ"uX4("w\buX4=b%nfe?bΟbX\"="neHƌʄ̎ƌ҄̎ƌڄ̎ƌ̎ƌ̎ƌ̎ƌ̎ƌ̎JH3|sCƌe8̎ ced"煟ɧ"cedbAɧb cb煟bc"A"'ݲPfeSݲPfe/5ed"(Aɧ"95edb@Nɧb/5b(Ab95"@N"J˟ݲPfe9퟿edPfe@N"95Z"JNbQh۟Zb[5edPfeJNɲZ"Qh۟o"b"[h۟Z"lbsZb}ieedPfe[h۟fd"3\"4˟=" 3޲O4Se"4#"" "$m͟dO/ퟪެb-~b.QKb,!ObiidCOCH3lS8̎wH3|sC'۟ɲZ8̎6yeBr8ιʄ̎8ι҄̎8ιڄ̎8ι̎8ι̎8ι̎8ι̎8ι̎XO5eH[uʄ̎[u҄̎[uڄ̎[u̎[u̎[u̎[u̎[u̎LMH3|sC[ue8̎ 'InQordertoavoidQtheovercrowdingQofsubstitution,youcanuseTU>'ExXprimitivecommandssuchas '\raiseUUand\kern.C'Example:'\steroid[fhm]{3A==HO;5B==H;{{10}B}==\lmoiety{H$_{3}$C};%'{{13}B}==\lmoiety{H$_{3}$C};%'{{14}A}==H;{{17}B}==\raise.5ex\hbox{COCH$_{3}$};%'{{17}SA}=={\kern.5em\lower1.5ex\hbox{H}}}C'TheseUUcommandsproGduce:ed"ɧ"edb]ɧbbb"]"ݭ+ݲPfeyoݲPfe;ed"]ɧ";edbɧb;b]b;""ݲPfe edPfe";Z"b-ZbşedPfeɲZ"-o"G՟"-Z""G՟b)aZb3.edPfe-fd"3ן\"-="z}b౟bKb"韬ھ"eN޲HOF;̎4z̎-̎&N̎FᲸ̎"̎̎ e̎FL`̎./=COCH3!o8̎+aH!o~̎"ßǢ̎#̎$kYބ̎%̎'̎( g58̎)~V̎ƷHy8̎ēH3|sCyɲZ8̎QeHǑʄ̎Ǒ҄̎Ǒڄ̎Ǒ̎Ǒ̎Ǒ̎Ǒ̎Ǒ̎-H3|sCǑe8̎ 'Themacro\steroidchain(carom.sty)istodrawasteroidderivqativewiththesidechain.9/Theformat 'ofUUthiscommandisasfollows: \steroidchain[BONDLIST]{SUBSLIST}'LoGcant?numbers?fordesignatingsubstitutionpositionsandbonddescriptorsforthesidechainarerepre-'sentedUUbythefollowingdiagram:#ŠObM'CHAPTERUU5.FUSEDTRICYCLICCARBOCYCLESANDSTEROIDSw<35'fe>|2. j@tAJdAJed"'lɧ"AJedb[(ɧbAJb'lbAJ"[("'ݲPfe:ݲPfeued"[(ɧ"uedbɧbub[(bu""[ݲPfeAԟedPfe䟧"uZ"Ŏ䟧b̨ŸZbuedPfeŎɲZ"̨Ÿo" "֨ŸZ" b~ZbLedPfe֨Ÿfd"3nPfe~"  g"~b\ gb *Pfe \KPfdP"C)T"CAT(sf22Sa(r)~جΟnrsf22Sb(lr)~جT.Tʟd23 \Kfd8dp23Sb(r) \ά )Ђd20Sa(l)hKfd8$dp20Sb(l) άTPTz24Sa(r) \T )TCz24\ -125KPfd8ܢdZc ΟdZd񦟇dZbj^dZaZe(CZf(CZgYff?ff:q(400,240) :q(0,0)>τffffff?('TheoKhandednessforeachorientedordouble-sidedpGositionisshownwithacharactersetinparentheses, 'whereUUthedesignationofovercrowdedUUpGositionsisabbreviated.> 'The>optionargumentBONDLIST>isbasedontheassignmentofcharacters(a{t)torespGectivebGonds'as6shownintheabGovediagramandT*able5.6.gTheloGcant-numbering6ofchaincarbGonsisalsodesignated'withtheBONDLISTintheformoftwo-characterindicators(Za{Zg)ascollectedinT*able5.8.#AbGond04L΍H*`T*ableUU5.8:qArgumentBONDLISTforchaincarbGons(nsteroidchain)4ML͉ff'UzfdCharacter?PrintedUUstructure)B ffCharacterjPrintedUUstructureff'UzZ=cnoUUaction- ff Za=c17,20-doubleUUbGond͟ ffZbP20,22-doubleUUbGondZc=c22,23-doubleUUbGond͟ ffZdP23,24-doubleUUbGondZe=c24,25-doubleUUbGond͟ ffZfP25,26-doubleUUbGondZg=c25,27-doubleUUbGond͟ ffff'Uz'moGdi er*intheargumentSUBSLIST)forn)=1{25*(exceptfusedpositionsandterminalpositionsnot'toybGespeci ed,e.g.,18)ycanbeoneofbondmodi ersshowninT*able2.2.3Ontheotherhand,abond'moGdi erSintheargumentSUBSLISTSforn=5,8,9,10,13,14,orS25(fusedpositionsetc.)mcanbe'selectedUUfrombGondmodi ersshowninT*able5.7. 'F*orJexample,the\steroidchainmacroprints(24RDz)-24-methyl-5 z-cholestan-3 -ol(campGestanol)and'5 z-lanostaneUUonlybyreplacingsubstituentsinargumentSUBSLIST.Thus,thestatements$'\steroidchain{3B==HO;5A==H;{{10}B}==\lmoiety{H$_3$C};9A==H;8B==H;%'{{17}SA}==\lower1ex\hbox{?H};{{13}B}==\lmoiety{H$_3$C};{{14}A}==H;%'{{20}SA}==H$_3$C;{{20}SB}==H;{{24}SA}==CH$_3$;{{24}SB}==H}'\steroidchain{4SB==\lmoiety{H$_3$C};4SA==CH$_3$;5A==H;%'{{17}SA}==\lower1ex\hbox{?H};%'{{10}B}==\lmoiety{H$_3$C};9A==H;8B==H;{{13}B}==\lmoiety{H$_3$C};%'{{14}A}==CH$_3$;{{20}SA}==\lmoiety{H$_3$C};{{20}SB}==H} 'typGesetUUthefollowingstructuraldiagrams:$%ĠObM'36BFUJIT*AUUShinsaku:qXMTU>'ExX'fe>|2$ mIed"Bɧ"SedbZ3ӟɧbIbBbS"Z3ӟ"dݲPfeAݲPfekMed"d3ӟɧ"uMedb|gɧbkMbd3ӟbuM"|g"4]ݲPfeuedPfe|g"uMZ"gbmZbN;edPfegɲZ"mo"K"mZ"Kb)ZbedPfemfd"3%ğ޲HO8㲪"5" JH4埡~̎<9Ǣ̎C̎JៜYބ̎R5̎Y̎`ݟ58̎h1~V̎a-Hcm̎cm̎cm ̎cm(̎cm0̎cm8̎cm@̎cmH̎U H3|sCcmɲZ8̎M韹H)ɲZ8̎r4 eHtKʄ̎tK҄̎tKڄ̎tK̎tK̎tK̎tK̎tK̎gǟeHʄ̎҄̎ڄ̎̎̎̎̎̎eH3|sCe8̎hPfe)ج"K g")b gbʛ՟PfeKPfdPWM)WTMAT嵟dH3|sC4埍~4̎4ݟ~4̎4՟~4̎4͟~4̎4ş~4̎4~4̎4~4̎4~4̎gdpHKέTgT豟zCH3h~̎o5f̎wIH̎~*̎΅Z ̎ύE̎ДЄ̎ћퟭ~̎ŸzHÛred"X<ɧ" redbɧbrbX<b r""XƟݲPfe% ݲPfe"֟ed"ɧ",֟edb3ɧb"֟bb,֟"3"=ݲPfe,redPfe3",֟Z"=bDْZbN`edPfe=ɲZ"Dْo"Up"NْZ"_pbg NZbpedPfeNْfd"3 ~H3|sCr>ʟğCH3 f̎ ̎ \ʄ̎ !튬̎)A̎0Xp̎7R̎?f4̎gboH_ ~̎`^Ǣ̎a̎bYބ̎cZ̎d̎e58̎fV~V̎rRH%̎%̎% ̎%(̎%0̎%8̎%@̎%H̎ p.H3|sC%ɲZ8̎:H=YNɲZ8̎)0eH,?pʄ̎,?p҄̎,?pڄ̎,?p̎,?p̎,?p̎,?p̎,?p̎KeCH3Ns,ʄ̎Ns,҄̎Ns,ڄ̎Ns,̎Ns,̎Ns,̎Ns,̎Ns,̎?ȟH3|sCNs,e8̎_>Pfeg Nج"_p g"q Nbx', gbPfe',KPfdP'|tr)'|TtrAT==ڟdH3|sC_ ~4̎]~4̎[~4̎Y~4̎Wꟍ~4̎U⟍~4̎Sڟ~4̎Qҟ~4̎OdpHYpέTX T 'ThefollowingexampleofdrawingcucurbitacinIillustratesthedesignationofdoublebGondsintheside 'chain.I Thus,a"singlemacroiscapableofcovering"awidevqarietyofderivativesbyalteringthedescription'inUUargumentsBONDLISTandSUBSLIST.'\steroidchain[ae{Zd}]{2==HO;3D==O;4Sb==\lmoiety{H$_3$C};4Sa==CH$_3$;%'9Sa==CH$_{3}$;{{11}D}==O;{{13}}==\lmoiety{H$_3$C};%'{{14}}==CH$_3$;{{20}Sa}==\lmoiety{H$_3$C};{{20}Sb}==HO;%'{{16}Sa}==OH;{{22}D}==O;{{25}}==OH}'proGducesed")ɧ"edbɧbb)b""ݲPfexݲPfeßed"ɧ"ßedbɧbßbbß""oݲPfeƑedPfe"ßZ"b-ZbMedPfeɲZ"-o"G]"-Z"G]b a;Zb. edPfe-fd"3,kɘ"("Ǔ_\b=bd֟òBHO)ɲZb'bן޲Oe"ǟ"_["_+ "]kH3|sC߱CH3TWT2qdOFެbFa~bƬKbĬşOb$OHa;Ffd8eCH3Ƒe8feٟeCH3Me8feH3|sCMe8fe+Pfe a;ج"G] g"a;b{ gb&G矡Pfe&{KPfdP:{i>_):{iT>_AT" ~zfeGsfOџ؄8feaA؄8feǟdH3|sCG%Kfd8L蟂dpHOG]άT TJ.۟1IJOH:{iKPfd8%5jObM2 'UChapter 62'TFiv8e- T{orLower-Memb ered'Carb ocycles:'6.1" DrawingffFive-Membs3eredCarbocycles'6.1.1&gVerticalFormsuT'Themacro\cyclopentanevandthecorrespGondinginversemacroareusedtodraw ve-membGeredcar- 'bGocyclicUUcompoundsofverticaltypGe(lowcycle.sty).qTheformatsofthesecommandsareasfollows:% \cyclopentanev[BONDLIST]{SUBSLIST} \cyclopentanevi[BONDLIST]{SUBSLIST}'The'followingdiagramsshowthenumbGeringofthecommandsfordesignatingsubstitutionpositions(1{5)'andUUbGonddescriptors(a{e):bw.tVdV"]+p"LbDbf>ݲPfeDĂݲPfeD匄fd"3731Sb(l)PNBZ+<1Sa(r)VTWDToƟ2Sb(r)g+p粪Th^鲪Tuޟ2Sa(r)g+p܄fd8oƟ3Sb(r)g+pɲZh^DzZuޟ03Sa(r)g+p匄fd8!4Sb(l)>ɲZT=dDzZTZ04Sa(l)6|匄fd8!5Sb(l)>粪=d鲪Z5Sa(l)6|܄fd8a[83a[t2U1GVt5GV84UMHcjXb_a<XdHegff?ff:q(400,240):q(0,0)>τffffff?q{trdredbɧb%XǟݲPfe% ݲPfe red"X=ɧ"X=܄fd"3'1Sb(l)redT >˟edTş1Sa(r)redked.?O2Sb(r)%ɲZ&IDzZ4?g02Sa(r)%匄fd8.?O3Sb(r)%粪T&I鲪T4?g3Sa(r)%܄fd874Sb(l)X=粪$鲪ٻ4Sa(l)X܄fd875Sb(l)X=ɲZT$DzZTٻ05Sa(l)X匄fd8r1u82ut3qߟt4qߟ85r?a(rkXbr?pc0e㑟XdSff?ff:q(400,240):q(0,0)>τffffff?R 'In'ExX'fe>|20=GoL΍7ͲT*ableUU6.1:qBONDLISTforcommandsncyclopentanevandncyclopentanehLebL͉ff$ۤfdCharacterpPrintedUUstructureff$ۡnone=cmotherUUnucleus a=c1,2-doubleUUbGondb=c2,3-doubleUUbGondc=c4,3-doubleUUbGondd=c4,5-doubleUUbGonde=c5,1-doubleUUbGondA=caromaticUUcirclefn+g=cplusUUatthen-nitrogenatom(n=1to5)f0+g=cplusUU(orminus)atthecenterff$ێl-" "-bObٟݲPfeyݲPfeO匄fd"3COOH؄8fe?òBCH3 ɲZ";'"q"#O"qb b-ݲPfe zaݲPfe 匄fd"3˟Ph?؄8fe:ჟòBPh-OɲZ"/'"g_-edb ɧbٟݲPfeyݲPfe-ed"Oɧ"O܄fd"3_feO_ßed8fe3ed8fe?òBPh ɲZ";'"qedb#Oɧb-ݲPfe zaݲPfeqed" ɧ" ܄fd"3˟Oaed8fewed8fe<0CH3-O匄fd86CH2|sCH2CO2CH3-OɲZ/DzZk 'ThezcommandiscapableoftypGesettingadelocalizedandalocalizedformofcyclopentadienylzanion 'asUUfollows.L'\cyclopentanev[A{0{$-$}}]{}?\qquad'\cyclopentanev[bd{1{\lower1.2ex\hbox{$-$}}}]{}'TheseUUstatementsproGduceds"5b"bb0ݲPfetݲPfe匄fd"3RNdr"" rbX=b%XǟݲPfe% ݲPfeX=匄fd"3" feqfe?]X捍'6.1.2&gHorizontalFormsW'Themacro\cyclopentanehandthecorrespGondinginversemacroareusedtodraw ve-membGeredcar-'bGocyclicUUcompoundsofhorizontaltypGe(lowcycle.sty).qTheformatsofthesecommandsareasfollows:'[ObM'CHAPTERUU6.FIVE-ORLOWER-MEMBEREDCARBOCYCLES)39'fe>|2  \cyclopentaneh[BONDLIST]{SUBSLIST} \cyclopentanehi[BONDLIST]{SUBSLIST}x)'ThefollowingdiagramsshowloGcantnumbGersfordesignatingsubstitutionpositionsaswellasbondde-'scriptorsUUforshowingdoublebGonds:f>.tFR`dh`Td^kTh`d^(UP^HfdPP^HLpfdPP+>"3fe~_1Sb(r)n`"p-"~_1Sa(r)n`bp2br^П2Sb(r)d^催"f^ȟŲO"b^B2Sa(lr)d+f傄8fe=B3Sa(lr)P+傄8fe(L3Sb(l)F^H催bD^ŲOb(Lr4Sb(l)F^H>"D^Lq"=344Sa(lr)P+v8fer^Пr5Sb(r)d^>bf^ȟLqbb^345Sa(lr)d+fv8feJ@cX bl@aleXdgff?ff:q(240,400):q(0,0)>τffffff?q{tq۟`dq۟`џkџfdPџLpfdPq۟`Tџ(UT">"3fe0Y3Sb(r)"!催"$QŲO" B3Sa(r)"傄8fe歅2Sb(l)џ催bŲObB2Sa(lr)傄8fe1Sb(l)q۟`bq-bڡ1Sa(l)q۟`"q2"0Yr4Sb(r)"!>b$QLqb 344Sa(r)"v8fe歅r5Sb(l)џ>"Lq"345Sa(lr)v8feqޟ@ar# b%rs@cr#deSff?ff:q(240,400):q(0,0)>τffffff?PV'inBwhichthesamemacroisusedtotypGesetbothsaturatedandunsaturatedderivqatives.EF*orBONDLIST,'seeUUT*able6.1.x)'Example:Jፑ'\cyclopentaneh{1==COOH;3==CH$_{3}$}\qquad\qquad'\cyclopentaneh{1==Ph;3==Ph}?\par'\cyclopentanehi[b]{1D==O;2==Ph}\qquad\qquad'\cyclopentanehi{1D==O;2Sb==CH$_{3}$;%'2Sa==CH$_{2}$CH$_{2}$CO$_{2}$CH$_{3}$}'proGduceUUthefollowingstructures:f>`)`T3kT`)`3(UfdPLpfdP߱>"3feCOOH`)2fd8BCH3催TߓT/am`T+wkT/am`+w(U'fdP'LpfdP>"3feEߟPh5am2fd8 BPh'催TןTY`kfdPLpfdP`T(UT>"3feefd}K]Oŵeʄfd8ŵZfd8BPh催TߓT 1`'k'fdP'LpfdP 1`T'(UT*E>"3feLOeʄfd8Zfd8x3CH3 '催b ŲObBCH2|sCH2CO2CH3傄8fe%o'6.2" DrawingffFfour-Membs3eredCarbocyclesoF'Themacro\cyclobutaneisacommandfordrawingfour-membGeredcarbocyclesbyusingthefollowing'formatUU(lowcycle.sty).Jፑ \cyclobutane[BONDLIST]{SUBSLIST}'LoGcantUUnumbersUU(1{4)andbonddescriptors(a{d)areshowninthefollowingdiagram:(fEObM'40BFUJIT*AUUShinsaku:qXMTU>'ExX'fe>|2 UAtAd̟Pfe|PfeA2fdPA2҄fdPTL2Sb(r)ATuNTl2Sa(r)A2҄fd8TK3Sb(r)APuNPlL&3Sa(r)A2fd8㨟L1Sb(l)A^1Sa(l)Av2҄fd8㨟K4Sb(l)APT^PTL&4Sa(l)Av2fd8AgAgA֟@cA֟aBbAdff?ff:q(400,240) :q(0,0)>τffffff? }'ThehandednessforeachorientedpGositionisshownwithacharactersetinparentheses.dTheoptional 'argumentUUBONDLISTspGeci esdoublebondsasshowninT*able6.2.w=L΍mCFT*ableUU6.2:qBONDLISTforcommandsncyclobutane./MٟL͉ffbfdCharacter_PrintedUUstructure(S ffCharactercPrintedUUstructureffbnone=cmotherUUskeleton(fullysaturated)͟ ffa=c1,2-doubleUUbGondP"+ ffbc2,3-doubleUUbGondc=c3,4-doubleUUbGondP"+ ffdc4,1-doubleUUbGondfn+g=cplusUUatthen-nitrogenatom(n=1to4)ffb펎) 'TheargumentSUBSLISTis lledintospGecifyeachsubstituentwithaloGcantnumbGerandabond'moGdi erUUshowninT*able2.2,inwhichnisanarabicnumeralbGetween1and4.'Example:1@ \cyclobutane{2Sa==CH$_{3}$;2Sb==CH=CH$_{3}$} \cyclobutane{3D==O} \cyclobutane{3Sa==OH;3Sb==CH$_{3}$}'proGduceUUthefollowingstructures:i$g=XPfe=Pfep:2fdPp:2҄fdP#CH3p2҄fd8#LCH=CH3pTڟTPfePfeϟ2fdPϟ2҄fdPS8OzQL"z""Բ"GꂟPfe32Pfe4d2fdP4d2҄fdPV"L&OHH2fd8P KCH3HPIQP)Hk'6.3" DrawingffThree-Membs3eredHeterocyclesȭ'Theumacro\cyclopropanefordrawingthreee-membGeredcarbocycleshasthefollowingformat(lowcy-'clo.sty). \cyclopropane[BONDLIST]{SUBSLIST}'Thus,>the9QloGcantnumbGering(1{2)andthebonddescription(a{c)arecommonasshowninthefollowing'diagram:)u:ObM'CHAPTERUU6.FIVE-ORLOWER-MEMBEREDCARBOCYCLESEu41'fe>|2 AtAdA֫AT֫TfdPc1Sb(l)A^[X1Sa(r)ATtT^2d2Sb(r)¬(Xèv22Sa(r)fd8}2d3Sb(l)¬ThTwX23Sa(l)fd8AgAgA֟aAcAHbff?ff:q(400,240) :q(0,0)>τffffff?'ThehandednessforeachorientedpGositionisshownwithacharactersetinparentheses.dTheoptional 'argumentUUBONDLISTiswrittendowntospGecifydoublebondsasshowninT*able6.3.?cL΍SET*ableUU6.3:qArgumentBONDLISTforcommandsncyclopropaneRfC5L͉ff5fdCharacterpnDPrintedUUstructureff5none=csaturateda=c1,2-doubleUUbGondb=c2,3-doubleUUbGondc=c3,1-doubleUUbGondA=caromaticUUcirclefn+g=cplusUUatthen-heteroatom(n=1to3)=cn=4UU{outerplusat1pGosition=cn=5UU{outerplusat2pGosition=cn=6UU{outerplusat3pGositionf0+g=cplusUUatthecenterofacyclopropaneringff5M" 'The ,argumentSUBSLIST isenteredtospGecifyeachsubstituentwithaloGcantnumbGerandabond'moGdi erUUshowninT*able2.2,inwhichnisanarabicnumeralbGetween1and3.>鍑'Example: \cyclopropane{2Sa==COOCH$_{3}$;2Sb==COOCH$_{3}$}\qquad \cyclopropane{2Sa==COOH;2Sb==COOH}\qquad\qquad \cyclopropane{3Sa==H$_{3}$C;3Sb==H$_{3}$C}>鍑'proGduceUUthefollowingstructures:e񳍍rŌw֫lŌThx֫ThxfdP,T2COOCH3|xfd8,<2dCOOCH3|x¬}6Οğ֫ΟTy؟֫Ty؟fdP-2COOHz(fd8-~2dCOOHz(¬xNS֫HTD{֫TD{fdP!ņ2H3|sC6zfd8(n2dH3|sC>{¬T=G̟T 'Thismacroisbasedonthemacro\threeheteroinwhichtheA*TOMLISTofthelattercommand'isUsetbGeforehand.'Inordertodrawacarbonatomonacyclopropanering, youcanusethecommand'\threeheteroUUinsteadof\cyclopropane.>鍑'Example:*4ObM'42BFUJIT*AUUShinsaku:qXMTU>'ExX'fe>|2  \threehetero[H]{1==C;2==C;3==C}% '{1Sa==H;1Sb==H;2Sa==COOCH$_{3}$;2Sb==COOCH$_{3}$;%g3Sa==H$_{3}$C;3Sb==H$_{3}$C}\qquad\qquad\qquad \threehetero[H]{2==C}{2Sa==COOH;2Sb==COOH}Y'proGduceUUthefollowingstructures:cjF:FRFTFTzfd Ȏ2ܲC2C2C֟HTTHX@,2COOCH3yfd (,2`COOCH3yeyenp2H3|sCyfd (s2`H3|sCy*eTyeT&r(ǒ& rTz|֫Tz|fd -Z2C?.:2COOH3z؟fd (:.&2`COOH3z؟e3ze!/'6.4" DrawingffIndaneDerivatives'6.4.1&gVerticalFormsofIndanes捑'SincePthemacros\indanevand\indaneviareincludedinthestyle le`lowcycle.sty',theyareintroGduced'here.qTheUUformatof\indanvis:wp \indanev[BONDLIST]{SUBSLIST}'TheVloGcantnumbGering(1{9)andthebonddescription(a{j)haveVacommonformatasshowninthe'followingUUdiagrams:ojǍ%tCşdv-ݲPfee"m _"[bTգbTqݲPfeTգ匄fd"3CşedbJգɧbCş"Jգ"9şed"2ɧ"9şb2b2nݲPfeQUfe9")ɘ"6]("9")\b6]=bsSfeb۟1(lr)eO؄8fe 2(r)w _㲪by b òB3(r)w _ɲZ"y '"wòB5(l)(ɲZb&'bw޲6(l)(㲪"&"@7(lr)C؄8fe@4(lr)Ced8feff?ff:q(400,240):q(0,0)>τffffff?tǗdEݲPfe4S"<1"*Sb#ub#CݲPfe#u匄fd"3ǗedbuɧbǗ"u"Ǘed"ɧ"ǗbbzݲPfe+1.S-91Sa(r)4ST6.TNȇ2Sb(r)F1粪TGH鲪TTȟ2Sa(r)F1܄fd8Nȇ3Sb(r)F1ɲZGHDzZTȟ03Sa(r)F1匄fd8O5Sb(l)ɲZTziDzZT05Sa(l)󭁟匄fd8O6Sb(l)粪zi鲪6Sa(l)󭁟܄fd8食7Sb(l) Ǘ GA7ǗTT食4Sb(l) ǗedT GedTA4Sa(r)Ǘed矽ed ϟ9#C8fe ϟ8#CɲZ8fe ԝ (Sa(r)& (Sb(l)ǻd&XjǻhSe.aXfog3wpcHXb=wa)ifޟff?ff:q(400,240):q(0,0)>τffffff?1'The8Mhandednessforeachorientedordouble-sidedpGositionisshownwithacharactersetinparenthe-'ses.dEachccharacterintheoptionalargumentBONDLISTNindicatesaspGeci cdoublebondasshownin'T*ableУ6.4.ThedefaultsettingofBONDLISTЄproGducesafullyunsaturatedstructure,wwhentheoption'BONDLISTfisφomitted.ZIfyouwanttodrawafullysaturatedstructure,youshouldwritedownanull'optionUU([])or[H]. ܍ 'TheV!argumentSUBSLISTUisusedtospGecifyeachsubstituentwithaloGcantnumbGerandabondmodi er'shown?inT*able2.2,CinwhichnisanarabicnumeralbGetween1and7.jSubstitutionon8(3apGosition)or'9UU(7apGosition)canbeassignedinthesameway*.Y'Example:wp \indanev{1D==O}?\qquad \indanev[H]{1D==S;2==COOH}\par \indanev[egj]{2D==O;3Sa==H;3Sb==Ph}\qquad \indanev[A]{2D==O;3Sa==H;3Sb==Ph}'proGduceUUthefollowingstructures:+ObM'CHAPTERUU6.FIVE-ORLOWER-MEMBEREDCARBOCYCLESEu43'fe>|20=GoL΍G_T*ableUU6.4:qArgumentBONDLISTforcommandsnindolevandothersL3"L͉ffY[fdCharacterTBPrintedUUstructureW| ff1Character+PrintedUUstructureffY[noneUUorr=caromaticUUsix-membGeredring͟ ff1HUUor[]$fullyUUsaturatedform a=c1,2-doubleUUbGond:)C ff1b$2,3-doubleUUbGondc=c3,3a-doubleUUbGond5)B ff1d$4,3a-doubleUUbGonde=c4,5-doubleUUbGond:)C ff1f$5,6-doubleUUbGondg=c6,7-doubleUUbGond:)C ff1h$7,7a-doubleUUbGondi=c1,7a-doubleUUbGond5)B ff1j$3a,4a-doubleUUbGondA=caromaticUUcircle(six-membGeredring)B=caromaticUUcircle( ve-membGeredUUring)fn+g=cplusUUatthen-nitrogenatom(n=1to9)ffY[l,卍5LݲPfeN"h~"Nb4ŸbݲPfe4Ÿ匄fd"3edb4Ÿɧb"4Ÿ"{ed"tɧ"{btbsԟݲPfefezHɘ"w|("zH\bw|=brfe4O6؄8feN؄8feGݲPfe6ן"=",ןb%b%XǟݲPfe%匄fd"3redbɧbr"" red"X=ɧ" rbX=b% ݲPfe31S5?m؄8fe7ݟ؄8feTCOOHG㲪bIbY"ݲPfeJ"("Jblb:ݲPfel匄fd"3ŎedblɧbŎ"l"|Ŏed"uɧ"|Ŏbubux~ݲPfe|+ɘ"y&("|+\by&=b_`fe\޲OZebƊb_b`& bƖ0H(匄fd8~Ph(ɲZFxDzZE؟ݲPfe4,"< "*,b#Nb#ݲPfe#N匄fd"3pedbNɧbp"N"ped"ɧ"pbbz`ݲPfe>崮S>޲OEτffffff?tǗd4Sedb<1ɧbEݲPfe#CݲPfe*Sed"#uɧ"#u܄fd"3ǗedbuɧbǗ"u"Ǘed"ɧ"ǗbbzݲPfe+1.SedT-edT91Sa(r)4Sed6.edNȇ2Sb(r)F1ɲZGHDzZTȟ02Sa(r)F1匄fd8Nȇ3Sb(r)F1粪TGH鲪TTȟ3Sa(r)F1܄fd8食4Sb(l) Ǘ GA4Sa(r)ǗTTO5Sb(l)粪zi鲪5Sa(l)󭁟܄fd8O6Sb(l)ɲZTziDzZT06Sa(l)󭁟匄fd8食7Sb(l) ǗedT GedTA7Ǘed矽ed ϟ8#C8fe ϟ9#CɲZ8feǻh&Xjǻdog.aXfSe=waHXb3wc)ifޟff?ff:q(400,240):q(0,0)>τffffff?t'The8Mhandednessforeachorientedordouble-sidedpGositionisshownwithacharactersetinparenthe-'ses;this{ishowever{omittedintheovercrowded{pGosition(between{7and1).LTheoptionalargument'BONDLISTUUspGeci esbondstobedoubledasshowninT*able6.4.AG'Example:,ObM'44BFUJIT*AUUShinsaku:qXMTU>'ExX'fe>|2  \indanevi{1D==O}?\qquad \indanevi[H]{1D==S;2==COOH}\par \indanevi[egj]{2D==O;3Sa==H;3Sb==Ph}\qquad \indanevi[A]{2D==O;3Sa==H;3Sb==Ph}č'proGduceUUthefollowingstructures:b덍Nedbh~ɧb5LݲPfeݲPfeNed"4Ÿɧ"4Ÿ܄fd"3edb4Ÿɧb"4Ÿ"{ed"tɧ"{btbsԟݲPfefezHɘ"w|("zH\bw|=brfe4O6ed8feNed8fe6ןedb=ɧbGݲPfe%XǟݲPfe,ןed"%ɧ"%܄fd"3redbɧbr"" red"X=ɧ" rbX=b% ݲPfe31S5?med8fe7ݟed8feTòBCOOHGɲZ"I'"Y`Jedb(ɧbݲPfe:ݲPfeJed"lɧ"l܄fd"3ŎedblɧbŎ"l"|Ŏed"uɧ"|Ŏbubux~ݲPfe|+\by&=b|+ɘ"y&("_`fe\òBOZ$"Ɗ"_˘"`&e"ƖH(܄fd8~Ph(粪TFx鲪T4,edb< ɧbE؟ݲPfe#ݲPfe*,ed"#Nɧ"#N܄fd"3pedbNɧbp"N"ped"ɧ"pbbz`ݲPfe>崮S>òBOE<$"Gl"Fa؟˘"Hbe"TxHF ܄fd8N`PhF 粪TGHZ鲪T鶍'6.4.2&gHorizontalFormsofIndanesuT'Thew@macro\indanehfordrawingindanederivqativesofhorizontaltypGehasthefollowingformat(lowcy-'cle.sty). \indaneh[BONDLIST]{SUBSLIST}'LoGcantnumbers(1{9)fordesignatingsubstitutionpositionsandbonddescriptors(a{j)arerepresented'byUUthefollowingdiagram:k%tCşdNfdPfVTb TfVb 'NKЄfdPMՉ"3feCş2|H fV2|Tb TCş2|TH[qTfV2|b [qNfdPP_ĘfdG TITb"`UџP_dfd| sf1(r)lV1fd8h #2(lr)b c<[A䢲3(lr)HTFkTAfP5(lr)HLZGUmLZh #fP6(lr)b LZTc<[LZT| sL"7(r)lVefd8$zL"4(l)5efd8ff?ff:q(400,800):q(0,0)>τffffff?tǗdfdP5aӟT1ݟT5aӟ1ݟ'KЄfdP["3feǗ2| 5aӟ2|T1ݟ TǗ2|T[qT5aӟ2|1ݟ[qfdPKE|1Sb(r);aӟ"=bˍ"KE1Sa(r);aӟb=b1b?`2Sb(r)1ݟ"3 "/՟䢲2Sa(lr)0᫟8feA`3Sb(l)b]b fI䢲3Sa(lr)[8feAL5Sb(l)LZ"]" fIfP5Sa(lr)[L8fe?L6Sb(r)1ݟLZb3 b/՟fP6Sa(lr)0᫟L8feKE87Sb(r);aӟ2|"=bI"KE27Sa(r);aӟ2|b=bebiu84Sb(l)Ǘ2|bgIb24Sa(l)Ǘ2|"ge"@O2D91ݟKЄfd8a2D8UKЄfd82\d$ߟ2(j8/2\h8/2g$ߟ2f{2e󲟱lc$ߟ8b8/la8/˼ifޟff?ff:q(400,800):q(0,0)>τffffff?x'TheoKhandednessforeachorientedordouble-sidedpGositionisshownwithacharactersetinparentheses.'TheUUoptionalargumentBONDLISTgivesthedescriptionofdoublebGondsasshowninT*able6.4.b'Example: \indaneh{1D==O}?\qquad \indaneh[H]{1D==S;2==COOH}\par \indaneh[egj]{2D==O;3Sa==H;3Sb==Ph}\qquad \indaneh[A]{2D==O;3Sa==H;3Sb==Ph}'proGduceUUthefollowingstructures:- ObM'CHAPTERUU6.FIVE-ORLOWER-MEMBEREDCARBOCYCLES)45'fe>|2 gڟfdP Th*T h*'gڟKЄfdP4"3fe2|gڟ  2|Th* T2|Tgڟ[qT 2|h*[qgڟfdP~ĘfdN(TTܟ~dfdhfO e*fd8 fd8fdP7 WT2aT7 W2a'KЄfdPߟ"3fer2| 7 W2|T2a Tr2|T[qT7 W2|2a[qfdPLɟfS= We*fd8= Wfd88yCOOH2a3򱟜{τffffff?qtrBdrB88fdP8KЄfdPrBT8'T2V"3ferB2|8 7 ~2|T2 TrB2|T8[qT7 ~2|2[q8fdP |1Sb(l) rBbrˍbY1Sa(l) rB"r1"쟗`2Sb(l)8bb 䢲2Sa(lr)8fe@`3Sb(r)2"4"0䢲3Sa(lr)2V8feL84Sb(r)= ~2|"? I"L24Sa(r)= ~2|b? eb@L5Sb(r)2LZb4b0fP5Sa(r)2VL8fe^L6Sb(r)8LZ"" fP6Sa(lr)L8fe 87Sb(l) rB2|brIbY27Sa(l) rB2|"re"Br2D82KЄfd8 ş2D9KЄfd8^2\h&r2(i:rڟ2\d:rڟ2e&r2f2B2g2Bla&r8b4lcҟ˼igȉff?ff:q(400,800):q(0,0)>τffffff?,'Example:< \indanehi{1D==O}?\qquad \indanehi[H]{1D==S;2==COOH}\par \indanehi[egj]{2D==O;3Sa==H;3Sb==Ph}\qquad \indanehi[A]{2D==O;3Sa==H;3Sb==Ph}'proGduceUUthefollowingstructures:.ObM'46BFUJIT*AUUShinsaku:qXMTU>'ExX'fe>|2 䟯gڟgڟfdPgڟKЄfdP䟹Tgڟ'T4"3fe2|gڟ  2|Th* T2|Tgڟ[qT 2|h*[qgڟfdP~ĘfdN(TTܟ~dfdmTfOwe*fd8wfd8rfdPKЄfdPrT'T2/"3fer2| 7 W2|T2a Tr2|T[qT7 W2|2a[qfdP0ofSq㟱e*fd8q㟮fd8ݟCOOHTTyŎfdPKЄfdPŎT'Tߢ"3feŎ2| _ʟ2|Tԟ TŎ2|T[qT_ʟ2|ԟ[qfdP,_ҟTžT(ĘfdP䢲O_N1T+1TXTT̟䢲Hߢ8fe `Phԟ""pfffdPfKЄfdPpTf'T0ᄟ"3fep2|f 5a2|T1 Tp2|Tf[qT5a2|1[qffdP\e2䢲Oa01T-1T:TꟜT/䢲H0ᄟ8fe?`Ph1"3柝"/ ObM2 'UChapter 72'TSix-Mem8b ered T{Heterocycles:'7.1" DrawingffVferticalFormsofSix-Membs3eredHeterocycles'7.1.1&gCommandsforSp`eci edUseuT'Themacro\pyridinevandtherelatedmacrosareusedtodrawsix-membGeredheterocycliccompoundsof 'verticaltypGe(hetarom.sty).HEachofthesecommandstypGesetsheterocycleswiththespeci carrangement'ofUUheteroatomsonitsskeleton.qTheformatsofthesecommandsareasfollows:\'\pyridinev[BONDLIST]{SUBSLIST}'\pyrazinev[BONDLIST]{SUBSLIST}'\pyrimidinev[BONDLIST]{SUBSLIST}'\pyridazinev[BONDLIST]{SUBSLIST}'\triazinev[BONDLIST]{SUBSLIST}'By]usingthecommand\pyridinevasanexample,themoGdeoflocantnumbGeringfordesignatingsub-'stitutionPpGositionsisshownasfollowsalongwiththebGonddescriptorsforassigninginnerdoublebonds:a.tVdYb]+pɧbH"Dɧ"V"]+p"LbDbf>ݲPfeDĂݲPfeKw\bH*=bH"H\"cdfeRexNR쟯1(lr)U`eX ,fet+òB2(r)g+pɲZ"i+'"t+޲3(r)g+p㲪bi+bR4(lr)U`؄8fe(iD5(l):㲪"8"(iDòB6(l):ɲZb8'bgff?ff:q(400,240):q(0,0)>τffffff?q{trd)bɧb "X=ɧ"r"" rbX=b%XǟݲPfe% ݲPfeXuexN'1Sb(l) GeXT /eXTş1Sa(r)>eX?eX.?O2Sb(r)%ɲZ&IDzZ4?g02Sa(r)%匄fd8.?O3Sb(r)%粪T&I鲪T4?g3Sa(r)%܄fd8'4Sb(l)r >˟ş4Sa(r)rTkT75Sb(l)X=粪$鲪ٻ5Sa(l)X܄fd876Sb(l)X=ɲZT$DzZTٻ06Sa(l)X匄fd8r1u82ut3r4qߟt5qߟ86r?a(rkXbr?ccfXe㽟dSff?ff:q(400,240):q(0,0)>τffffff?z 'The@optionalargumentBONDLIST@spGeci esbondstobedoubledasshowninT*able7.1.4Sincea'spGeci ccharacterisassignedtoaspeci cbondofeachheterocycle,!theconcretemeaningofthechar-'acterisdi erentfromoneheteroGcycletoanother.However,*themethoGdologyiscommonindrawingall'heteroGcyclesUUsothatthecommandsofXMTU>'ExXareeasytouse. 'The"argumentSUBSLISTshowseachsubstituentwithaloGcantnumbGerandabondmodi ershown'inUUT*able2.2,inwhichnisanarabicnumeralbGetween1and6.qF*orexample,thestatements,'\pyridinev{2==Cl;6==Cl;4==F}'\pyrazinev{2==Cl;6==Cl}'\pyrimidinev{2==Cl;6==Cl;4==F}'\pyridazinev{6==Cl;4==F}'\triazinev{2==Cl;6==Cl;4==F}'proGduceUUthefollowingstructures:K470ムObM'48CFUJIT*AUUShinsaku:XMTU>'ExX'fe>|2H=GWL΍P T*ableUU7.1:qArgumentBONDLISTforcommandsnpyridinev,etc.XebL͉ff$ۤfdCharacterpPrintedUUstructureff$ۡnoneUUorr=cpyridineUU(right-handed) l=cpyridineUU(left-handed)HUUor[]=cfullyUUsaturatedringa=c1,2-doubleUUbGondb=c2,3-doubleUUbGondc=c4,3-doubleUUbGondd=c4,5-doubleUUbGonde=c5,6-doubleUUbGondf=c6,1-doubleUUbGondA=caromaticUUcirclefn+g=cplusUUatthen-nitrogenatom(n=1to6)ff$ێjEbkɧboE"kɧ"|ō"k"rōbkb9ݲPfekx}ݲPfer+\bo%=boE"oEW"__feyexNߟòBClkɲZ"ߛ'"TzòBClaɲZb_'byF|[؄8feFݟbୟɧbF"Ϭɧ"Fݟ"P"FbyPb{ݲPfeyݲPfeFebFebF"F"`feݭ)Nݭ)exNòBClୟɲZ"ݟ'"òBClŬɲZbì'bHHbKɧb7H"33ɧ"D"Ha֫":b33bUٲ@fe3{ݲPfe:.u\b7=b7H"7G۟"Raٲ ffeAkexNRHGNb#òBClUɲZ"W'"òBCl)3ɲZb''bAkFDߟ؄8feY`F<bFdbF "Pɧ"." ".bPbڟݲ<feyݲPfe,\bƟ=bF "E"` ffeexNFd0NòBClPɲZb 'bF؄8feG~bNɧbGb"ɧ"p"a@֫"pb-֫b#ٲ@fez`ٲ@fe-ԟ\b-\bGb"G:" aBٲ ffeʟexN GN9N0႟òBCl#NɲZ"%~'"]òBClɲZbb'bʟF>؄8fe# 'ItshouldbGenotedthatthedefaultsettingoftheBONDLISTYistodepictafullyunsaturatedring '(usuallyBanaromaticring).:Bysettinganappropriatecharacterstring,asiglemacroisusedtotypGeset'bGoth7partiallysaturatedandunsaturatedderivqatives.lMoreover,ůa7fullysaturatedringcanbeobtained'byWsettinganullargumentorHHinBONDLIST.ThisspGeci cationcanbeillustratedwiththefollowing'examples.'\pyridinev[be]{1==H;2==Cl;6==Cl;4D==O}\qquad'\pyridinev[ce]{1==H;4==Cl;6==Cl;2D==O}\qquad'\triazinev[H]{2D==O;4D==O;6D==O;1==H;3==H;5==H}'proGduceUUthefollowingstructures:aJEbkɧboE"kɧ"|ō"k"rōbkb9ݲPfekx}ݲPfe__fenWfeyexNy矯H|[eX ,feߟòBClkɲZ"ߛ'"TzòBClaɲZb_'byO{_#؄8fe}œ؄8feFݟbୟɧbF"Ϭɧ"ϟ"ୟ"ϟbϬb{ݲPfeyݲPfe`k\"7="ƙfeݭ)exNݭ)HeX ,feݭ)Cl؄8feòBClŬɲZbì'bòBOߟ$""-{˘"-e"HHbKɧb7H"33ɧ"D"Ha֫":b7.A֫bUٲ@fe3{ٲ@feAkexNRHGN/ڟNb#òBOU!$"WQ"V.˘"X.e"AkOCa؄8feE؄8feòBO)$b'џb)ae˘b'a5ebAkHDߟeX ,fec'HXbX#b-޲H&'"&" 'InUUordertodepictachargeonanitrogen,youwritethestatements,forexample:1ObM'CHAPTERUU7.SIX-MEMBEREDHETEROCYCLES|49'fe>|2 '\pyridinev[r{1+}]{1==H;2==Cl;6==Cl;4==F}\qquad '\pyrazinev[l{1+}{4+}]{1==H;4==H;2==Cl;6==Cl}]ߍ'ThenUUyouobtainthefollowingstructures:aQF<b ɧbF "Pɧ"." ".bPbڟݲPfeyݲPfe,\bƟ=bF "E"`feR+exNHeX ,fe@òBCl ɲZ"<'"òBClPɲZb 'bF؄8feG~bNɧbGb"ɧ"G~"P"Gbbz^Pb#ݲPfez`ݲPfeG~bGbG~e"Ge":fe+2+ʟNʟexNʟH>eX ,feʟH>؄ ,fe0႟òBCl#NɲZ"%~'"]òBClɲZbb'b'InWthesecases,X#acharacter`r'or`l'shouldbGeaddedtotheargumentBONDLIST,sincethedefaultsare'hiddenUUbywritingothercharactersintheBONDLIST.3'7.1.2&gCommandsforGeneralUseuT'Theoxcommand\sixheterovisageneralmacrousedtodrawsix-memeredheteroGcyclicderivqativesof'vertical_typGe(hetarom.sty).ItisespGeciallyusefultodrawheteroGcycliccompoundshavingotherskeletal'atomsUUthannitrogenatoms.qTheformatofthiscommandisasfollows: \sixheterov[BONDLIST]{ATOMLIST}{SUBSLIST}'LoGcantr9numbersr9fordesignatingsubstitutionpositionsandcharactersforbond-descriptionareshownin'theUUfollowingdiagram:aQA6tA֟db bȟ""" "ȟbb(ٲ ,feƟٲ ,fe(04(0ex1 02 3065c⟯1Sb(l)ueXTtꟼeXT[1Sa(r)eXŸeX2Sb(r)[2D[؟2D"02Sa(r)[匄fd (3Sb(r)[2T[؟2T"3Sa(r)[܄fd (c4Sb(l)ut[4Sa(r)TŸT5Sb(l)'2'ԟ2{X5Sa(l)'ğ܄fd (6Sb(l)'2DT'ԟ2DT{X06Sa(l)'ğ匄fd (AaB&XbAc3xfϿXexd͟ff?ff:q(400,240):q(0,0)>τffffff?6 'EachcharactersetinparenthesesrepresentsthehandednessofthecorrespGondingposition, whichis xed'inUUthistypGeofmacrosbecauseofthelackofspacestoprintotherwise. 'TheYoptionargumentBONDLIST?isancharacterstringinapairofbrackets,whereeachcharacter'indicates7thepresenceofadoublebGondattheedgespeci edbythecharacter.gThebGond-speci cation7is'rather.arbitraryinsomecasesbutconformstochemicalconventionsasfaithfullyaspGossibleifsuchcon-'ventions>arepresence(T*able7.2).j1Sincethedefaultprintsafullyunsaturatedform,Canoptionargument'[H]UUshouldbGewrittentotypesetasaturatedform. 'TheaugumentA*TOMLISTsisalistofheteroatoms,5te.g.,1==Nforanitrogenatomat1-pGosition.'ItٴshouldbGeemphasizedthat,inordertotypesetaheteroatomatagivenposition,theedgesincident'to|theheteroatomareautomaticallytruncatedtoputspaceforprintingtheheteroatrom.Comparethe'followingUUexamples. 'TheargumentSUBSLISTforthismacrotakesageneralformat,pinwhichthemoGdi erslistedinT*able'2.2UUareused..'Example:'\sixheterov[H]{1==O}{2D==O;6D==O;3==CH$_{3}$;5==CH$_{3}$}\qquad'\sixheterov[b]{1==O}{}\qquad'\sixheterov[H]{3==O;5==O}{4D==O;6B==ICH$_{2}$;2B==CH$_{3}$}\qquad'\sixheterov[H]{3==S;5==S}{4Sa==SiMe$_{3}$;4Sb==Li}2ObM'50BFUJIT*AUUShinsaku:qXMTU>'ExX'fe>|2H=GWL΍-²T*ableUU7.2:qArgumentBONDLISTforcommandsnsixheterovandnsixheteroviXebL͉ff$ۤfdCharacterpPrintedUUstructureff$ۡnoneUUorr=csixheteroUU(right-handed) l=csixheteroUU(left-handed)HUUor[]=cfullyUUsaturatedforma=c1,2-doubleUUbGondb=c2,3-doubleUUbGondc=c4,3-doubleUUbGondd=c4,5-doubleUUbGonde=c5,6-doubleUUbGondf=c6,1-doubleUUbGondA=caromaticUUcirclefn+g=cplusUUatthen-nitrogenatom(n=1to6)ff$ێ!Jҍ'proGduceiʍNDbQʟɧb=Dޟ"9ɧ"J"Qʟ"@b9b[ݲPfe9wܟݲPfeGFexOhòBO[$"],"\+˘"^+ȟe"$㼟òBO/ܟ$b-b/^@˘b-^ebh޲CH3[ʟ㲪b]bu޲CH3/㲪"-ޟ"F<b ɧbF "Pɧ"." ".bPbڟݲPfeyݲPfe`feexOpedbNɧbped"ɧ"p"a@֫"pb-֫b#ٲ@fez`ٲ@fe GOOʟOa؄8fev؄8fe۔òBICH2ɲZbb'b0႟òBCH3#NɲZ"%~'"vȲedb}␟ɧblȲed"eԟɧ"vȲ"zb֫"lȲbi.֫b^ٲ@fee{ٲ@feHScBSz\SiMe3vȲTwTiPLipȲob; 'It7shouldbGenotedthatthesamecompoundcanbedrawnindi erentways.Thisfactisobvious 'bGecause|allthecommands,\pyridinev,\pyrazinev,\pyrimidinev,\pyridazinev,and|\triazinev,'areUUbasedonthemacro\sixheterov.;'Example:'\pyridinev[H]{1==H;4D==O;2==CH$_{3}$;6==CH$_{3}$}\qquad'\raisebox{1.5cm}{\em?vs.}\qquad'\sixheterov[H]{1==N}{1==H;4D==O;2==CH$_{3}$;6==CH$_{3}$}?\par'\bigskip'\pyridinev[be]{1==H;4D==O;2==CH$_{3}$;6==CH$_{3}$}\qquad'\raisebox{1.5cm}{\em?vs.}\qquad'\sixheterov[be]{1==N}{1==H;4D==O;2==CH$_{3}$;6==CH$_{3}$}'proGduceiʍݟbTɧb" ɧ":ϟ"T":ϟb b!{ݲPfeݲPfe!)exN!)HeX ,fe!)Oe؄8fe:՟؄8feTòBCH3TɲZ"Tݟ'"keòBCH3 ɲZb 'b;qR%vs.'ݟb+lɧb"8ɧ"$Rϟ"+l"Rϟb8b59{ݲPfeݲPfe!9)exN!9)H$eX ,fe!9)O"e؄8fe%R՟؄8feBlòBCH35lɲZ"7lݟ'"eòBCH3 8ɲZb8'b3ObM'CHAPTERUU7.SIX-MEMBEREDHETEROCYCLES|51'fe>|2 uݟbTɧb" ɧ":ϟ"T":ϟb b!{ݲPfeݲPfeԡfe:fe!)exN!)HeX ,fe!)Oe؄8fe:՟؄8feTòBCH3TɲZ"Tݟ'"keòBCH3 ɲZb 'b;qR%vs.'ݟb+lɧb"8ɧ"$Rϟ"+l"Rϟb8b59{ݲPfeݲPfe1졟feRfe!9)exN!9)H$eX ,fe!9)O"e؄8fe%R՟؄8feBlòBCH35lɲZ"7lݟ'"eòBCH3 8ɲZb8'b 'Thecommand\sixheteroviisageneralmacrousedtodrawsix-memeredheteroGcyclicderivqatives 'ofUUinverseverticaltypGe(hetarom.sty).qTheformatofthiscommandisasfollows:Y \sixheterovi[BONDLIST]{ATOMLIST}{SUBSLIST}'LoGcantnumbers(1{6)fordesignatingsubstitutionpositionsandbonddescriptors(a{f)areshowninthe'followingUUdiagram:fA6tA֟db bȟ""" "ȟbb(ٲ ,feƟٲ ,fe(01(0ex4 03 2056c1Sb(l)ut[1Sa(r)TŸT2Sb(r)[2T[؟2T"2Sa(r)[܄fd (3Sb(r)[2D[؟2D"03Sa(r)[匄fd (c⟯4Sb(l)ueXTtꟼeXT[4Sa(r)eXŸeX5Sb(l)'2DT'ԟ2DT{X05Sa(l)'ğ匄fd (6Sb(l)'2'ԟ2{X6Sa(l)'ğ܄fd (AaB&XbAc3xfϿXexd͟ff?ff:q(400,240):q(0,0)>τffffff? 'Thefollowingexamplesaretheonesinwhichthe\sixheterovcommandsintheabGoveexamplesare'replacedUUby\sixheterovi.'Example:Y'\sixheterovi[H]{1==O}{2D==O;6D==O;3==CH$_{3}$;5==CH$_{3}$}\qquad'\sixheterovi[b]{1==O}{}\qquad'\sixheterovi[H]{3==O;5==O}{4D==O;6B==ICH$_{2}$;2B==CH$_{3}$}\qquad'\sixheterovi[H]{3==S;5==S}{4Sa==SiMe$_{3}$;4Sb==Li}'proGducefJedbQʟɧb@ed"9ɧ"ND"RP"=Dޟb9wڟPb[ݲPfe9wܟݲPfeGFOhO[eb],b\+b^+ȟ bhòBCH3[ʟɲZ"]'"$㼟޲O/ܟe"-"/^@"-^ "uòBCH3/ɲZb-ޟ'b.edb ɧb.ed"Pɧ"F<"@P"F byPbڟݲPfeyݲPfe`feOpedba@ǎYbped"-ǎY"p"N"pbb#ݲ<fez`ݲ<fe G0O0OʟOaed8feved8fe0႟CH3#N㲪b%~b۔޲ICH2㲪"b"vȲedbzbǎYblȲed"i.ǎY"vȲ"}␟"lȲbeԟb^ݲ<fee{ݲ<feH0ScB0Sz\SiMe3vȲedwediPLipȲedTobedT 'Thecommands\sixheterovand\sixheterovicanyieldtheequivqalentresultsifthemoGdesof'numbGeringUUarealteredinA*TOMLISTandSUBSLIST.Forexample,thefollowingtwostatementsY'\sixheterov[H]{4==S}{1D==O}?\qquad'\sixheterovi[H]{1==S}{4D==O}'proGduceUUthesamestrucureasfollows.4$lObM'52BFUJIT*AUUShinsaku:qXMTU>'ExX'fe>|2 uedb5bɧbed"ɧ""hP"vbrPb0ݲPfetݲPfeޟSޟOed8feed8feredbɧb red"X=ɧ")"-P" b% Pb%XǟݲPfe% ݲPfeXuSXuO ed8fer!ed8fe4'However,NtheM0latterispreferredtotheformerbGecausethenumberingM0oftheringatomscomformstothe 'chemicalUUnomenclature.qThisisthereasonwhywehavemadesuchmacrosofinversetypGe.!.l'7.2" DrawingffHorizontalFformsofSix-Membs3eredHeterocycles)'7.2.1&gCommandsforSp`eci edUseb'The\macro\pyridinehandtherelatedmacrosareusedtodrawsix-membGeredheterocycliccompounds'ofUUhorizontaltypGe(hetaromh.sty).qTheformatsofthesecommandsareasfollows:'\pyridineh[BONDLIST]{SUBSLIST}'\pyrazineh[BONDLIST]{SUBSLIST}'\pyrimidineh[BONDLIST]{SUBSLIST}'\pyridazineh[BONDLIST]{SUBSLIST}'\triazineh[BONDLIST]{SUBSLIST}'The~followingdiagramsshowthenumbGeringfordesignatingsubstitutionpositionsaswellasthebond'spGeci cationUUforplacingdoublebonds:c*tBB`dDwPF^8[DwpTF^8(eTd~`T`^kTd~``^(UL^8fdPL^8LpfdP`x:^NGČTG؟TNܟefd@YۙN"ϔ1(l)4 2fd (?^B2(lr)F^8催TE*Tf^B3(lr)`^催a؟z^4(r)j~2fd8f^345(lr)`^>Ta؟>T?^346(lr)F:>E>gff?ff:q(240,400):q(0,0)>τffffff?qtq`d [P [ [pT (eT+ '`T&1kT+ '`&1(UfdPLpfdPۙNɟ1Sb(l)qߟ2bq2bޢ1Sa(l)qߟ4"q4"ꭕ2Sb(l)催bŲObB2Sa(lr)傄8fe4i3Sb(r)&1催"(aŲO"$)B3Sa(lr)&傄8fe@4Sb(r)1 '`"3 W-"@4Sa(r)1 '`b3 W2b4ir5Sb(r)&1>b(aLqb$)345Sa(lr)&v8feꭕr6Sb(l)>"Lq"346Sa(lr)v8fe qh1r82!u83*vh4r6!u5q@ar3 b.r@c.rdr3ecfW"ff?ff:q(240,400):q(0,0)>τffffff?a'EachVmacrocanbGeusedtotypGesetbothsaturatedandunsaturatedderivqatives.sF*orexample,V=thestate-'ments,'\pyridineh{2==Cl;6==Cl;4==F}'\pyrazineh{2==Cl;6==Cl}'\pyrimidineh{2==Cl;6==Cl;4==F}'\pyridazineh{6==Cl;4==F}'\triazineh{2==Cl;6==Cl;4==F}'proGduceUUthefollowingstructures:[c+Pe[c+pTe(eT_Y`TckT_Y`c(UkfdPkLpfdP,}_)fxgTfTmefd_E4ۙN^ߟBCle催TcßT^ߞ34Cle>d^ş>˟F_Y2fd8,Pu[,pTu(eTKPTş[TKpş(eufdPuLpfdPqz%yɟTҭT٭efd`ۙNFۙNABClu催T%TA34Clѓw>`'>;.QP=ן[;.QpT=ן(eT[b`TY{kT[b`W'(UCןfd@CןLpfdPW.ٟUa>{+T>wTE{efd f7GۙNTN6BCl=ן催T;ᇟT634Cl=ٟ>qFab2fd855ؠObM'CHAPTERUU7.SIX-MEMBEREDHETEROCYCLES|53'fe>|2 U,>P_Ӫ,>pTğ(eT` `TkT` `(Uԟfd@ğLpfdP,Ɵ_ڟyTdTԟefd fEۙNN34ClƟ>_v>|F` 2fd8-P&[-pT&(eT%al`T#zkT%al`#z(U &fd@ &Lpfd@!.( ܟvzzTƟTʟefd fGGۙNjNjNNBCl&催T֟T34Cl(>`؟>;ޟF+al2fd8㍑ 'Themacro\pyridinehiandtherelatedmacrosareusedtodrawsix-membGeredheterocycliccom- 'pGoundsUUofinverseUUhorizontaltypGe(hetarom.sty).qTheformatsofthesecommandsareasfollows:'\pyridinehi[BONDLIST]{SUBSLIST}'\pyrazinehi[BONDLIST]{SUBSLIST}'\pyrimidinehi[BONDLIST]{SUBSLIST}'\pyridazinehi[BONDLIST]{SUBSLIST}'\triazinehi[BONDLIST]{SUBSLIST}'TheInumbGeringfordesignatingsubstitutionpositionsandthebondspeci cationareshowninthefollowing'diagrams:b *tBB`dBB`F^8kBB`TF^8(UTbEPT`^[TbEp`^(eL^8fdPL^8LpfdP^4^FDTHrTNܟefddfۙNz^1(r)m2fd ,f^B2(lr)`^催a؟?^B3(lr)F^8催TE*T"ϔ4(l)4 2fd8?^345(lr)F:>E>f^346(lr)`^>Ta؟>Tgff?ff:q(240,400):q(0,0)>τffffff?qtq`dq` kq`T (UT(PT&1[T(p&1(efdPLpfdP+ ۙNɟ4Sb(l)q`bq-bޢ4Sa(l)q`"q2"ꭕ3Sb(l)催bŲObB3Sa(lr)傄8fe4i2Sb(r)&1催"(aŲO"$)B2Sa(lr)&傄8fe@1Sb(r)4 32"4 [2"@1Sa(r)4 34b4 [4b4ir6Sb(r)&1>b(aLqb$)346Sa(lr)&v8feꭕr5Sb(l)>"Lq"345Sa(lr)v8fe(@cr3 b.r@a.rfr3e㵟dW"ff?ff:q(240,400):q(0,0)>τffffff?'Eachw%macrocantypGesetbothsaturatedandunsaturatedderivqatives,wherethedefaultproducesafully'unsaturatedUU(aromatic)one.qF*orexample,thestatements,'\pyridinehi{2==Cl;6==Cl;4==F}'\pyrimidinehi{2==Cl;6==Cl;4==F}'\pyridazinehi{6==Cl;4==F}'\triazinehi{2==Cl;6==Cl;4==F}'proGduceUUthefollowingstructures:Zꍍ*l`/bk*l`T/b(UTJ8PTI[TJ8pI(e5bfdP5bLpfdPG^Gx.T0ĜT7efdM^ۙNOʟBClI催JEܟF42fd8Oʞ34ClI>TJE>TΟ`TkΟ`Tğ(UTPT[Tp(eԟfd@ğLpfdPytTTԟefd f_ۙNN,BCl催Fd>FŖ2fd8,34Cl>TFd>T0`&k0`T&(UT"PT"ǰӪT"p!v(e &fd@ &LpfdP"z֟tT`Tʟefd f%aTۙNjN쌠F2fd8'34Cl!v>T"GƟ>TnȒ`pknȒ`Tp(UT^PT؟[T^p؟(e}fd@}Lpfd@|8r֟Ts/"vT}efd fbۙNtǟNtǟNNBCl؟催I(XF`Z2fd834Cl؟>TI(>T"'7.2.2&gCommandsforGeneralUseuT'Themacro\sixheterohisageneralusercommandfordrawingsix-membGeredheterocyclesofhorizontal'typGeUU(hetaromh.sty).qTheformatofthiscommandisasfollows: \sixheteroh[BONDLIST]{ATOMLIST}{SUBSLIST}'LoGcant numbers fordesignatingsubstitutionpositionsaswellasbonddescriptorsareshowninthe'followingUUdiagram:6H5ObM'54BFUJIT*AUUShinsaku:qXMTU>'ExX'fe>|2 uA5tA`dPQӪpTQSTuaPTBӪTuapBSfd 0Lpfd 0۹ۙ4Aۙ1ʟ2ϟ3ʟN6ϟN5ps1Sb(l)A2bAa2bps1Sb(l)A4"Aa4"|};2Sb(l)(vb'vbGB2Sa(lr)[Yn (feǏ3Sb(r)v"v"ӟB3Sa(lr)[n ,feӏC4Sb(r)ݟ2"2"ӏC4Sa(r)ݟ4b4bǏr5Sb(r)JbJbӞ345Sa(lr)[~ ,fe}}?r6Sb(l)(J"'J"G346Sa(lr)[Yz (feA@aAݟ bB-@cB-dAݟe3_fΟff?ff:q(240,400) :q(0,0)>τffffff?'EachcharactersetinparenthesesrepresentsthehandednessofthecorrespGondingposition, whichis xed 'inBthistypGeofmacros.:TheSUBSLISTBandtheBONDLISTformatareshowninT*able2.2and7.2,'respGectivey*.'Example:Ao'\sixheteroh[H]{1==O}{2D==O;6D==O;3==CH$_{3}$;5==CH$_{3}$}\qquad'\sixheteroh[b]{1==O}{}\qquad'\sixheteroh[H]{3==O;5==O}{4D==O;6B==CH$_{2}$I;2B==CH$_{3}$}\qquad'\sixheteroh[H]{3==S;5==S}{4Sa==SiMe$_{3}$;4Sb==Li}'proGduceZ4v-*ܟP/b[-*ܟpT/b(eTM^`TIkTM^`I(U5bfdP5bLpfdP(fۙO(.BO.^,2PT-*ܟ2PT06ƘT/ĘT(.34O.^,p-*ܟp06f /f OʟBCH3I催JEOʞ34CH3I>TJE>T,>Pğ[,>pTğ(eT` `TkT` `(UğfdPğLpfdPhefdȟۙO0`&k0`T&(UT%al`T#zkT%al`#z(U &fd@ &Lpfd@j厲OjNO;ޟO+aleʄfd8+alZfd834CH2|sI(>`؟>(>`؟>BCH3&傭T֟TnȒ`sknȒ`Ts(UTbΟ`T|HkTbΟ`|H(Uyfd@yLpfd@̟厲S̟NS@SiMe3bΟ`bb2b@LibΟ`"b-" 'Themacro\sixheterohiisusedtodrawsix-membGeredhetrocyclesofinversehorizontaltypGe(het-'aromh.sty).qTheUUformatofthiscommandisasfollows: \sixheterohi[BONDLIST]{ATOMLIST}{SUBSLIST}'The'followingdiagramshowsloGcantnumbGers(1{6)fordesignatingsubstitutionpositionsalongwithbond'descriptorsUU(a{f)forsettingdoublebGonds.bύA6tA`dPRӪpTRSTubPTBӪTubpBSfd 0Lpfd 0ۺۙ1Aۙ4˟3П2˟N5ПN6zt4Sb(l)A2bAb2b{q4Sa(l)A4"Ab4"}<3Sb(l)(vb'vbHB3Sa(lr)[Zn (feя2Sb(r)ǎv"Ǐv"ԟB2Sa(lr)[n ,feݏD1Sb(r)ޟ2"2"ݏD1Sa(r)ޟ4b4bяr6Sb(r)ǎJbǏJbԞ346Sa(lr)[~ ,fe}@r5Sb(l)(J"'J"H345Sa(lr)[Zz (feӟ@cAޟ bB.@aB.fAޟe`d͟ff?ff:q(240,400):q(0,0)>τffffff?'EachcharactersetinparenthesesrepresentsthehandednessofthecorrespGondingposition, whichis xed'inthistypGeofmacros.uTheSUBSLISTandtheBONDLISTformatareshowninT*able2.2andTable'7.2,UUrespGectivey*.'Example:'\sixheterohi[H]{1==O}{2D==O;6D==O;3==CH$_{3}$;5==CH$_{3}$}\qquad'\sixheterohi[b]{1==O}{}\qquad'\sixheterohi[H]{3==O;5==O}{4D==O;6B==ICH$_{2}$;2B==CH$_{3}$}\qquad'\sixheterohi[H]{3==S;5==S}{4Sa==Me$_{3}$Si;4Sb==Li}7\ObM'CHAPTERUU7.SIX-MEMBEREDHETEROCYCLES|55'fe>|2 'proGduceZ*l`/bk*l`T/b(UTJ8PTI[TJ8pI(e5bfdP5bLpfdPM^ۙOOʟBOI2PJ82PG+DƘH^Ę(.BCH3/b催T-TOʞ34OIpTJ8pTG+Df TH^f T(.34CH3/d>.^>Ο`ğkΟ`Tğ(UTPT[Tp(eğfdPğLpfdPhefd_ۙO0`k0`T(UT%al`T!vkT%al`!v(U6fd@6Lpfd@H厲OHNOLOeʄfd8Zfd8'BCH3!v傭"GƟ'34ICH2!v>T"GƟ>TnȒ`pknȒ`Tp(UTbΟ`T؟kTbΟ`؟(U}fd@}Lpfd@v厲SvNSDMe3|sSidȒ`"bb2"VLidȒ`bbb-b8pUObM'56BFUJIT*AUUShinsaku:qXMTU>'ExX'fe>|29uObM2C܍'UChapter 829Ǎ'TFiv8e- T{orLower-Memb ered'Hetero cycles:9Ǎ'8.1" DrawingffVferticalFormsofFive-Membs3eredffHeterocyclesR'8.1.1&gCommandsforSp`eci edUseۍ'Themacro\pyrrolevandtherelatedmacrostypGeset ve-membGeredheterocycliccompoundsofvertical 'typGeUU(hetarom.sty).qTheformatsofthesecommandsareasfollows: \pyrrolev[BONDLIST]{SUBSLIST} \pyrazolev[BONDLIST]{SUBSLIST} \imidazolev[BONDLIST]{SUBSLIST} \isoxazolev[BONDLIST]{SUBSLIST} \oxazolev[BONDLIST]{SUBSLIST}U'The~followingdiagramsshowthenumbGeringfordesignatingsubstitutionpositionsaswellasthebond'spGeci cationUUforwritingdoublebonds:cC.tVdY"]^P"HbDĀPbf>ݲPfeDĂݲPfeD匄fd"3cdfeH\feRNR1(lr)U`؄ ,fet+2(r)g+p㲪bi+bt+òB3(r)g+pɲZ"i+'"(iDòB4(l):ɲZb8'b(iD޲5(l):㲪"8"gff?ff:q(400,240):q(0,0)>τffffff?q{trd)"-P" b% Pb%XǟݲPfe% ݲPfeX=匄fd"3XuN'1Sb(l) G /ş1Sa(r)>T?T.?O2Sb(r)%粪T&I鲪T4?g2Sa(r)%܄fd8.?O3Sb(r)%ɲZ&IDzZ4?g03Sa(r)%匄fd874Sb(l)X=ɲZT$DzZTٻ04Sa(l)X匄fd875Sb(l)X=粪$鲪ٻ5Sa(l)X܄fd8u83ut2r1qߟt5qߟ84r?MHc(rkXbr?aXe㽟dSff?ff:q(400,240):q(0,0)>τffffff? 'EachxofthemacrosiscapableoftypGesettingbothsaturatedandunsaturatedderivqatives.3(Theoptional'argumentf=BONDLISTespGeci esbondtobedoubledasshowninT*able8.1.Thedefaultsettingisto'proGduce afullyunsaturatedring;iontheotherhandanullaugumentorH inBONDLISTproGducesa'fullyUUsaturatedring. 9Ǎ 'TheV!argumentSUBSLISTUisusedtospGecifyeachsubstituentwithaloGcantnumbGerandabondmodi er'shownUUinT*able2.2,inwhichnisanarabicnumeralbGetween1and5.qF*orexample,thestatements,'\pyrrolev{1==H;2==COOH;5==CH$_{3}$}\qquad\qquad\qquad'\pyrazolev{1==H;3==Ph;5==Ph}\qquad'\imidazolev{1==H;2==CH$_{3}$}Kβ57:vFObM'58BFUJIT*AUUShinsaku:qXMTU>'ExX'fe>|20=GoL΍RT*ableUU8.1:qArgumentBONDLISTforcommandsnpyrrolev,etc.LebL͉ff$ۤfdCharacterpPrintedUUstructureff$ۡnone=cmotherUUnucleus HUUor[]=cfullyUUsaturatedforma=c1,2-doubleUUbGondb=c2,3-doubleUUbGondc=c4,3-doubleUUbGondd=c4,5-doubleUUbGonde=c5,1-doubleUUbGondA=caromaticUUcirclefn+g=cplusUUatthen-nitrogenatom(n=1to5)ff$ێ"'\isoxazolev{3==CH$_{3}$}\qquad '\oxazolev{2==CH$_{3}$}"'proGduceUUthefollowingstructures:alE"pP"[E}bWxyPby7ݲPfeWx{ݲPfeW匄fd"3v_]feZUfeeNeHhY؄ ,feߝCOOHyi㲪b{ߙb7v!޲CH3M㲪"K}"Fߟ"G"FßbyPb}ٲ@feyݲPfe匄fd"3`ٲ ffeƛfe+NGN+H؄ ,feòBPh௟ɲZ"ߟ'"PK޲Ph٬㲪"׬ß"\H!"`%P"KHbG{Pbiݲ<feG{ݲPfeG5匄fdxfa ffeJݟfeUmNfHI0NUmHX؄ ,fev%CH3i㲪bk!bY`F<"Fd"F byPbڟٲ@feyݲPfeP匄fd"3`ٲ ffefeOFdN@òBCH3 ɲZ"<'"G~"P"Gbbz^Pb#ݲ<fez`ݲPfe匄fdx aB ffe:feʟO G0N0႟CH3#N㲪b%~b 'The#macro\pyrroleviandtherelatedmacrosareusedtodraw ve-membGeredheterocycliccom-'pGoundsUUofinverseUUverticaltypGe(hetarom.sty).qTheformatsofthesecommandsareasfollows: \pyrrolevi[BONDLIST]{SUBSLIST} \pyrazolevi[BONDLIST]{SUBSLIST} \imidazolevi[BONDLIST]{SUBSLIST} \isoxazolevi[BONDLIST]{SUBSLIST} \oxazolevi[BONDLIST]{SUBSLIST}'TheUUloGcantnumbGeringandthebondspeci cationareshowninthefollowingdiagrams.a.tVdYb]+pɧbf>ݲPfeDĂݲPfeH"Dɧ"D܄fd"3cdfeH\feRexNR쟯1(lr)U`eX ,fet+òB2(r)g+pɲZ"i+'"t+޲3(r)g+p㲪bi+b(iD޲4(l):㲪"8"(iDòB5(l):ɲZb8'bgff?ff:q(400,240):q(0,0)>τffffff?q{trd)bɧb%XǟݲPfe% ݲPfe "X=ɧ"X=܄fd"3XuexN'1Sb(l) GeXT /eXTş1Sa(r)>eX?eX.?O2Sb(r)%ɲZ&IDzZ4?g02Sa(r)%匄fd8.?O3Sb(r)%粪T&I鲪T4?g3Sa(r)%܄fd874Sb(l)X=粪$鲪ٻ4Sa(l)X܄fd875Sb(l)X=ɲZT$DzZTٻ05Sa(l)X匄fd8r1u82ut3qߟt4qߟ85r?a(rkXbr?pc0e㑟XdSff?ff:q(400,240):q(0,0)>τffffff?;ObM'CHAPTERUU8.FIVE-ORLOWER-MEMBEREDHETEROCYCLESu59'fe>|2  'TheUUargumentsBONDLISTandSUBSLISThavethesameformatsasabGove(T*ables8.1and2.2).c'Example:ƍ'\pyrrolevi{1==H;2==COOH;5==CH$_{3}$}\qquad\qquad\qquad '\pyrazolevi{1==H;3==Ph;5==Ph}\qquad'\imidazolevi{1==H;2==CH$_{3}$}\par'\isoxazolevi{3==CH$_{3}$}\qquad'\oxazolevi{2==CH$_{3}$}'proGduceUUthefollowingstructures:`퍍lEboiɧby7ݲPfeWx{ݲPfe[E}"Wɧ"W܄fd"3v_]feZUfeeexNe埯HhYeX ,feߝòBCOOHyiɲZ"{ߙ'"7v!òBCH3MɲZbK}'bFߟbGb}ݲ<feyݲPfeFß"ɧ"܄fd"3` ffeƛfe+exNG0N+HeX ,fePh௟㲪bߟbPKòBPh٬ɲZb׬ß'b\H!b_ɧbiٲ@feG{ݲPfeKH"G5ɧ"G5܄fdxfaٲ ffeJݟfeUmexNfHINUmHX៼eX ,fev%òBCH3iɲZ"k!'"Y`F<bFdbڟݲ<feyݲPfeF "Pɧ"P܄fd"3` ffefeexOFd0N@CH3 㲪bτffffff?'EachcharactersetinparenthesesrepresentsthehandednessofthecorrespGondingposition, whichis xed'inUUthistypGeofmacros. 'TheoptionargumentBONDLISTkisacharacterstringinapairofbrackets,Iowhereeachcharacter'indicatesUUthepresenceofadoublebGondattheedgespeci edbythecharacter(T*able8.2). 'SincethedefaultofBONDLISTprintsafullysaturatedform,8the\fiveheterovrequiresnooption'argumentUU[H]incontrastto\sixheterov. 'TheargumentSUBSLISTforthismacrotakesageneralformat,pinwhichthemoGdi erslistedinT*able'2.2UUareused.c'Example:<ObM'60BFUJIT*AUUShinsaku:qXMTU>'ExX'fe>|2$=G{L΍(?ŲT*ableUU8.2:qArgumentBONDLISTforcommandsnfiveheterovandnfiveheteroviFebL͉ff$ۤfdCharacterpPrintedUUstructureff$ۡa=c1,2-doubleUUbGond b=c2,3-doubleUUbGondc=c4,3-doubleUUbGondd=c4,5-doubleUUbGonde=c5,1-doubleUUbGondA=caromaticUUcirclefn+g=cplusUUatthen-nitrogenatom(n=1to6)f0+g=cplusUU(orminus)atthecenterff$ێe'\fiveheterov{1==O}{2D==O;5D==O;3==CH$_{3}$;4==CH$_{3}$}\qquad '\fiveheterov[b]{1==O}{}\qquad'\fiveheterov{2==O;5==O}{1D==O;3B==CH$_{2}$CH$_{3}$;4B==CH$_{3}$}\qquad'\fiveheterov{2==S;5==S}{1Sa==SiMe$_{3}$;1Sb==Li}e'proGduceaND"RP"=Dޟb9wڟPb[ݲPfe9wܟݲPfe9匄fd"3GFOhO[eb],b\+b^+ȟ bhòBCH3[ʟɲZ"]'"$㼟޲O/ܟe"-"/^@"-^ "uòBCH3/ɲZb-ޟ'bF<"@P"F byPbڟݲPfeyݲPfeP匄fd"3`feOp"a@֫"pb-֫b#ٲ@fez`ٲ@fe匄fd"3 GOOʟOa؄8fev؄8fe0႟òBCH2|sCH3#NɲZ"%~'"xòBCH3ɲZbb'bvȲ"zb֫"lȲbi.֫b^ٲ@fee{ٲ@feeԟ匄fd"3HScBSz\SiMe3vȲTwTiPLipȲob 'The^macro\fiveheteroviisemployed^todraw ve-membGeredheterocycliccompoundsofinverse 'verticalUUtypGe(hetarom.sty).qTheformatofthiscommandisasfollows: \fiveheterovi[BONDLIST]{ATOMLIST}{SUBSLIST}'TheUUfollowingdiagramshowsthenumbGeringfordesignatingsubstitutionpositions:A6tA֟db b(ٲ ,feƟٲ ,feȟ""[<܄fd4(0ex1 0205 34c⟯1Sb(l)ueXTtꟼeXT[1Sa(r)eXŸeX2Sb(r)[2D[؟2D"02Sa(r)[匄fd (3Sb(r)[2T[؟2T"3Sa(r)[܄fd (4Sb(l)'2'ԟ2{X4Sa(l)'ğ܄fd (5Sb(l)'2DT'ԟ2DT{X05Sa(l)'ğ匄fd (AaB&XbApceLXd͟ff?ff:q(400,240) :q(0,0)>τffffff?󒍑 'The~#optionalargumentBONDLIST~spGeci esdoublebondsasshowninT*able8.2,Vwhereanycombi- 'nationUUofcharacters(a{d)enablesustodrawbGothsaturatedandunsaturatedderivqatives. 'TheHargumentSUBSLIST)spGeci eseachsubstituentwithaloGcantnumbGerandabondmodi ershown'inUUT*able2.2,inwhichnisanarabicnumeralbGetween1and5. 'Example:e'\fiveheterovi{1==O}{2D==O;5D==O;3==CH$_{3}$;4==CH$_{3}$}\qquad'\fiveheterovi[b]{1==O}{}\qquad'\fiveheterovi{2==O;5==O}{1D==O;3B==CH$_{2}$CH$_{3}$;4B==CH$_{3}$}\qquad'\fiveheterovi{2==S;5==S}{1Sa==SiMe$_{3}$;1Sb==Li}=ޠObM'CHAPTERUU8.FIVE-ORLOWER-MEMBEREDHETEROCYCLES61'fe>|2 'proGduceeญNDbQʟɧb[ݲPfe9wܟݲPfe=Dޟ"9ɧ"9܄fd"3GFexOhòBO[$"],"\+˘"^+ȟe"h޲CH3[ʟ㲪b]b$㼟òBO/ܟ$b-b/^@˘b-^ebu޲CH3/㲪"-ޟ"F<b ɧbڟݲPfeyݲPfeF "Pɧ"P܄fd"3`feexOpedba@ǎYb#ݲ<fez`ݲ<feped"-ǎY"܄fd"3 G0O0OʟOaed8feved8fe0႟CH2|sCH3#N㲪b%~bx޲CH3㲪"b"vȲedbzbǎYb^ݲ<fee{ݲ<felȲed"i.ǎY"eԟ܄fd"3H0ScB0Sz\SiMe3vȲedwediPLipȲedTobedT$'8.2" DrawingBHorizontalFformsofFive-Membs3eredHeterocyclesCۍ'8.2.1&gCommandsforSp`eci edUse'The-macro\pyrrolehandtherelatedmacrosareusedtodraw ve-membGeredheterocycliccompounds 'ofUUhorizontaltypGe(hetaromh.sty).qTheformatsofthesecommandsareasfollows:푍 \pyrroleh[BONDLIST]{SUBSLIST} \pyrazoleh[BONDLIST]{SUBSLIST} \imidazoleh[BONDLIST]{SUBSLIST} \isoxazoleh[BONDLIST]{SUBSLIST} \oxazoleh[BONDLIST]{SUBSLIST}2-'TheUUfollowingdiagramsshowthenumbGeringfordesignatingsubstitutionpositions:.tFR`dfEPTd^[TfEpd^(eP^HfdPP^HLpfdPP+>"3feRefdRfdizۙN~_1(r)q2fd ,j^B2(r)d^催eC^B3(lr)J^H催TI*TC^344(lr)JJ>I>j^345(r)d^>Te>Tgff?ff:q(240,400):q(0,0)>τffffff?q{tq۟`d$PT"![T$p"!(eџfdPџLpfdP>"3fe( ۙN<1Sb(r)0 #2"0 K2"<1Sa(r)0 #4b0 K4b0Y2Sb(r)"!催"$QŲO" B2Sa(lr)"傄8feB3Sa(lr)傄8fe歅3Sb(l)џ催bŲOb歅r4Sb(l)џ>"Lq"344Sa(lr)v8fe0Yr5Sb(r)"!>b$QLqb 345Sa(lr)"v8fe @cr# b*rs@a*rser#dSff?ff:q(240,400):q(0,0)>τffffff? Z 'F*orUUBONDLIST,seeTable8.2.qForexample,thestatements,푍'\pyrroleh{1==H;2==COOH;5==CH$_{3}$}\qquad\qquad\qquad'\pyrazoleh{1==H;3==Ph;5==Ph}\qquad'\imidazoleh{1==H;2==CH$_{3}$}?\par'\isoxazoleh{3==CH$_{3}$}\qquad'\oxazoleh{2==CH$_{3}$}2-'proGduceUUthefollowingstructures:xPTw[Txpw(ecAfdPcALpfdPb>"3feeefdefd|_sۙNH_2fd ,}BCOOHw催xE}34CH3w>TxE>T]PTӪT]pן(efd@LpfdPU>"3fe+efd f+fd`ۙN˟N?H`ٟ2fd ,SBPh催T7T 34Phן>TG'>ThPTg[Thpg(eWٟfd@SɟLpfdPRᗟ>xfeWٟefd fUmfdlaۙNNNHtb2fd ,m1BCH3g催hHi>ObM'62BFUJIT*AUUShinsaku:qXMTU>'ExX'fe>|2 uPTnӪTp4(efd@LpfdP߲>"3feefd ffd`ۙO(NBCH3催TߔT"PT!v[T"p!v(e6fd@ &LpfdP >xfe6efd fʟfd&aXۙOeN'BCH3!v催"GƟT捑 'The#macro\pyrrolehiandtherelatedmacrosareusedtodraw ve-membGeredheterocycliccom- 'pGoundsUUofinverseUUhorizontaltypGe(hetaromh.sty).qTheformatofthiscommandisasfollows:q3 \pyrrolehi[BONDLIST]{SUBSLIST} \pyrazolehi[BONDLIST]{SUBSLIST} \imidazolehi[BONDLIST]{SUBSLIST} \isoxazolehi[BONDLIST]{SUBSLIST} \oxazolehi[BONDLIST]{SUBSLIST}'The͊loGcantnumbGeringfordesignatingsubstitutionpositionsandthebondspeci cationforsettingdouble'bGondsUUareshowninthefollowingdiagram:cdZ.tFR`dHwŸPJ^H[P^HfdPP^HLpfdPHwŸpTJ^H(eTd+f>"3feRefdRfdCeۙN&Ϥ1(l)82fd (C^B2(lr)J^H催TI*Tj^B3(r)d^催ej^344(r)d^>Te>TC^345(lr)JJ>I>gff?ff:q(240,400):q(0,0)>τffffff?q{tq۟`dKPџ[џfdPџLpfdPKpTџ(eT">"3feۙN0Y3Sb(r)"!催"$QŲO" B3Sa(r)"傄8fe歅2Sb(l)џ催bŲObB2Sa(lr)傄8fe1Sb(l)qϟ2bq2bڡ1Sa(l)qϟ4"q4"0Yr4Sb(r)"!>b$QLqb 344Sa(r)"v8fe歅r5Sb(l)џ>"Lq"345Sa(lr)v8feqޟ@ar# b%rs@cr#deSff?ff:q(240,400):q(0,0)>τffffff?- 'F*orUUexample,thestatements,q3'\pyrrolehi{1==H;2==COOH;5==CH$_{3}$}\qquad\qquad\qquad'\pyrazolehi{1==H;3==Ph;5==Ph}\qquad'\imidazolehi{1==H;2==CH$_{3}$}\par'\isoxazolehi{3==CH$_{3}$}\qquad'\oxazolehi{2==CH$_{3}$}'proGduceUUthefollowingstructures:cdZ[+P]A[cAfdPcALpfdP[+pT]A(eTv_>"3feeefdefdVE^ۙNA؟HJ2fd (V BCOOH]A催T[TV 34CH3]C>\^>-P`MӪfd@LpfdP-pT(eTय़>"3feefd f+fdFۙNƟN͓HY2fd ( BPhן催G'S34Ph铉>`9>K.CPMɟ[Sɟfd@SɟLpfdPK.CpTMɟ(eTf>xfeUmefd fUmfdFGۙNd N1`H:Ǜ2fd (FBCH3Mɟ催TKyTY,^P_Ӫfd@LpfdP,^pT(eT>"3feefd ffdۙO#NLBCH34催F-P&[ &fd@ &LpfdP-pT&(eT D>xfeʟefd fʟfd&ۙOjNBCH3&催T֟T?=ObM'CHAPTERUU8.FIVE-ORLOWER-MEMBEREDHETEROCYCLESu63'fe>|2 '8.2.2&gCommandsforGeneralUseuT'Thecommand\fiveheterohisageneralmacrousedtodraw ve-memeredheteroGcyclicderivqativesof 'horizontalUUtypGe(hetaromh.sty).qTheformatofthiscommandisasfollows:q \fiveheteroh[BONDLIST]{ATOMLIST}{SUBSLIST}'TheUUloGcantnumbGersfordesignatingsubstitutionpositionsarerepresentedbythefollowingdiagram:`ĘA6tA`dubPTBӪTubpBSfd 0Lpfd 0[Z4fe۾ۙ1˟3П2˟N4ПN5ݏD1Sb(r)ޟ2"2"ݏD1Sa(r)ޟ4b4bя2Sb(r)ǎv"Ǐv"ԟB2Sa(lr)[n ,feHB3Sa(lr)[Zn (fe}<3Sb(l)(vb'vb}@r4Sb(l)(J"'J"H344Sa(lr)[Zz (feяr5Sb(r)ǎJbǏJbԞ345Sa(lr)[~ ,fe՟@cAޟ bB.@aB.eAޟd͟ff?ff:q(240,400):q(0,0)>τffffff?'EachcharactersetinparenthesesrepresentsthehandednessofthecorrespGondingposition, whichis xed'inUUthistypGeofmacros. 'TheYoptionargumentBONDLIST?isancharacterstringinapairofbrackets,whereeachcharacter'indicatesEothepresenceofadoublebGondattheedgecorrespondingtothecharacter(T*able8.2).BThe'argumentA*TOMLISTvlistsasetofatomsplacedontheedgesassigned.yTheargumentSUBSLISTvfor'thisUUmacrotakesageneralformat,inwhichthemoGdi erslistedinT*able2.2areused.踍'Example:'\fiveheteroh{1==O}{2D==O;5D==O;3==CH$_{3}$;4==CH$_{3}$}\qquad'\fiveheteroh[b]{1==O}{}\qquad'\fiveheteroh{2==O;5==O}{1D==O;3B==CH$_{2}$CH$_{3}$;4B==CH$_{3}$}\qquad'\fiveheteroh{2==S;5==S}{1Sa==SiMe$_{3}$;1Sb==Li}'proGduce`ĘZxPTY[TZxpY(eEfdPELpfdPDp>"3fe^^ԟۙO_ BOY(2PZx2PW+ƘX^ԟĘ8nBCH3?催T=RT_ 34OY(pTZxpTW+f TX^ԟf T8n34CH3?>>^T>PT4[Tp4(efdPLpfdP߲>"3feefd`ۙO%al`T#zkT%al`#z(U &fd@ &Lpfd@ >"3fej厲OjNO;ޟO+aleʄfd8+alZfd8BCH2|sCH3&傭T֟T34CH3(>`؟>(>`؟>b`T|(kTb`|((Uqhfd@qhLpfd@p6>"3fe厲SNS SiMe3b`bbޟ2b Lib`"bޟ-" 'Thecommand\fiveheterohiisageneralmacrofordrawing ve-memeredheteroGcyclicderivqatives'ofUUinversehorizontaltypGe(hetaromh.sty).qTheformatofthiscommandisasfollows: \fiveheterohi[BONDLIST]{ATOMLIST}{SUBSLIST}'The~followingdiagramshowsthenumbGeringfordesignatingsubstitutionpositionsaswellasthebond'spGeci cationUUforwritingdoublebonds:`ĘA6tA`dPRӪfd 0Lpfd 0pTRST[4feAۙ1˟2П3˟N5ПN4я3Sb(r)ǎv"Ǐv"ԟB3Sa(r)[n ,fe}<2Sb(l)(vb'vbHB2Sa(lr)[Zn (fezt1Sb(l)A2bAb2b{q1Sa(l)A4"Ab4"яr4Sb(r)ǎJbǏJbԞ344Sa(r)[~ ,fe}@r5Sb(l)(J"'J"H345Sa(lr)[Zz (feA@aAޟ bB.@cAޟdӟe͟ff?ff:q(240,400):q(0,0)>τffffff?@ObM'64CFUJIT*AUUShinsaku:XMTU>'ExX'fe>|2 'Example:o'\fiveheterohi{1==O}{2D==O;5D==O;3==CH$_{3}$;4==CH$_{3}$}\qquad '\fiveheterohi[b]{1==O}{}\qquad'\fiveheterohi{2==O;5==O}{1D==O;3B==CH$_{2}$CH$_{3}$;4B==CH$_{3}$}\qquad'\fiveheterohi{2==S;5==S}{1Sa==Me$_{3}$Si;1Sb==Li}'proGduceUUthefollowingstructures:`=+P?[EfdPELpfdP=+pT?(eTX>"3fe7ۙO8nBO>^l2PT=+2PT@vƘT?&ĘT_ BCH3Y催ZEB8n34O>^lp=+p@vf ?&f _ 34CH3Y>TZEB>T,^P[fdPLpfdP,^pT(eT>"3feefdۙO0`k6fd@6Lpfd@0`T(UT D>"3feH厲OHNOLOeʄfd8Zfd8'BCH2|sCH3!v傭"GƟ'34CH3!v>T"GƟ>Tfr`hkuxfd@uxLpfd@fr`Th(UT↟>"3fenn厲SnnNS<ßMe3|sSi\r`"ZB2"N Li\r`bZB-b A'8.3" DrawingffFfour-Membs3eredHeterocycles'The macro\fourheteroisacommandforgeneraluse,Swhichiscapableofgivingskeletalatomsas'anA*TOMLIST.Thismacroisdesignedfordrawingfour-membGeredheterocyclesbyusingthefollowing'formatUU(hetarom.sty). \fourhetero[BONDLIST]{ATOMLIST}{SUBSLIST}'TheUUloGcantnumbGeringiscommoninthesecommandsasshowninthefollowingdiagram:lƍ.ˮtVkdiމ ,feU9 ,feZD2fd ȎZD2҄fd ȎfxL&3TL&4fx|2T|1x2(r)mǟfbmfbx83(r)mǟј"mј"8Բ1(l)I_f"I7f"884(l)I_јbI7јbg`ff?ff:q(400,240):q(0,0)>τffffff?qRtqd? ,fe> ,fe62fd Ȏ62҄fd ȎؚL&3 L&4ؚ|2 |1%L2Sb(r)rNTrfT#%2Sa(r)rN2҄fd (%K3Sb(r)rN:rf:#%L&3Sa(r)rN2fd (L1Sb(l)qqΟע 1Sa(l)q2҄fd (K4Sb(l)q:TqΟ:Tע L&4Sa(l)q2fd (qRgqg r@c rarRbq֟dS9ff?ff:q(400,240):q(0,0)>τffffff?p 'TheoKhandednessforeachorientedordouble-sidedpGositionisshownwithacharactersetinparentheses.'TheUUoptionalargumentBONDLISTisusedforthebGondspeci cationshowninT*able8.3.r1L΍?T*ableUU8.3:qArgumentBONDLISTforcommandsnfourheteroandothers.*1eL͉ffm*դfdCharactere*PrintedUUstructure-pd ff9CharacterPrintedUUstructureffm*աnone=cmotherUUcompGound(fullysaturated)͟ ff a=c1,2-doubleUUbGondZ[ ff9b2,3-doubleUUbGondc=c3,4-doubleUUbGondZ[ ff9d4,1-doubleUUbGondfn+g=cplusUUatthen-nitrogenatom(n=1to4)ffm*Վq 'The2argumentA*TOMLIST2takesausualformatwithrespGecttoheteroatomsattachedton=1to4,'e.g.,UU1==Nforanitrogenatomat1-pGosition. 'TheV!argumentSUBSLISTUisusedtospGecifyeachsubstituentwithaloGcantnumbGerandabondmodi er'shownUUinT*able2.2,inwhichnisanarabicnumeralbGetween1and4.8'Example:AObM'CHAPTERUU8.FIVE-ORLOWER-MEMBEREDHETEROCYCLES65'fe>|2  \fourhetero{1==N}{1==H} \fourhetero{1==O}{3Sa==COOH;3Sb==COOH} \fourhetero{1==O;2==O}{3Sa==COOH;3Sb==COOH} 0'proGduceUUthefollowingstructures:aW=XPfe=@fep:2fdP~2҄fd |NwHp.f"pf"Pfe@feϟ2fdP2҄fd ܙY|OzL&COOH2fd8zuKCOOHPoPGꂟ@fe32@fe4d2fdP8P2҄fd ȎD |O/|OV"L&COOHH2fd8P KCOOHHPIQP ܢ'8.4" DrawingffThree-Membs3eredHeterocycles'Themacro\threeheterofordrawingthreee-membGeredheterocycleshasthefollowingformat(het-'arom.sty). \threehetero[BONDLIST]{ATOMLIST}{SUBSLIST}'TheUUloGcantnumbGeringiscommonasshowninthefollowingdiagram:m.ˮtVkdYyYL]TLETOfd ȎRş2ܲ1\S22J^23Rş1(lr)U9؄ ,fem2(r)bџR"bR".6媲3(l)>iRb>ARbg`ff?ff:q(400,240):q(0,0)>τffffff?qRtqdT̟TX@fd ȎXL2ܲ1>ڟ22231Sb(l)1Sa(r)>ƟT>ޟTئ2`2Sb(r) %Xe %peغ22Sa(r) %Xfd (2`3Sb(l)$eT$؟eTU23Sa(l)$ȟfd (qRgqg raqʟcqHbS9ff?ff:q(400,240):q(0,0)>τffffff?] 'TheoKhandednessforeachorientedordouble-sidedpGositionisshownwithacharactersetinparentheses.'TheUUoptionalargumentBONDLISTspGeci esdoublebondsasshowninT*able8.4.cL΍<߲T*ableUU8.4:qArgumentBONDLISTforcommandsnthreeheteroandothersRfC5L͉ff5fdCharacterpnDPrintedUUstructureff5none=csaturated a=c1,2-doubleUUbGondb=c2,3-doubleUUbGondc=c3,1-doubleUUbGondA=caromaticUUcirclefn+g=cplusUUatthen-heteroatom(n=1to3)=cn=4UU{outerplusat1pGosition=cn=5UU{outerplusat2pGosition=cn=6UU{outerplusat3pGositionf0+g=cplusUUatthecenterofacyclopropaneringff5э 'The2argumentA*TOMLIST2takesausualformatwithrespGecttoheteroatomsattachedton=1to3,'e.g.,UU1==Nforanitrogenatomat1-pGosition.BObM'66BFUJIT*AUUShinsaku:qXMTU>'ExX'fe>|2  'TheargumentSUBSLISTydescribGeseachsubstituentwithaloGcantnumbGerandabondmodi ershown 'inUUT*able2.2,inwhichnisanarabicnumeralbGetween1and3.'Example: \threehetero{1==N}{1==H;2Sa==COOCH$_{3}$;2Sb==COOCH$_{3}$}\qquad \threehetero{1==O}{2Sa==COOH;2Sb==COOH}\qquad\qquad \threehetero{1==S}{3Sa==H$_{3}$C;3Sb==H$_{3}$C}'proGduceUUthefollowingstructures:b'w¬ub:<hxTjx:{¬T=G̟TCObM2 'UChapter 92'THetero cycles T{withFused'Six-Mem8b ered T{Rings:'9.1" DrawingffVferticalForms'9.1.1&gCommandsforSp`eci edUseuT'The,¯o\quinolinevisusedtodrawquinolinederivqativesofverticaltypGe(hetarom.sty).d Macrosfor 'drawingUUotherfusedheteroGcyclesarealsode ned.qTheformatsofthesecommandsareasfollows:獑 \quinolinev[BONDLIST]{SUBSLIST} \isoquinolinev[BONDLIST]{SUBSLIST} \quinoxalinev[BONDLIST]{SUBSLIST} \quinazolinev[BONDLIST]{SUBSLIST} \cinnolinev[BONDLIST]{SUBSLIST} \pteridinev[BONDLIST]{SUBSLIST}'LoGcantjnumbersjfordesignatingsubstitutionpositionsaswellasbonddescriptorsforsettingdoublebonds'areUUshowninthefollowingdiagram:n>%tCşdiobm _ɧbv-ݲPfee"m _"Xos"Tգɧ"[bTգbTqݲPfeCşedbJգɧbCş"Jգ"9şed"2ɧ"9şb2b2nݲPfeiobiobf\"i"="9")\b6]=b9")ɘ"6]("QUfeb۟exNb۟1(lr)eOeX ,fe òB2(r)w _ɲZ"y '" ޲3(r)w _㲪by bb۟4(lr)eO؄8fe@5(lr)C؄8few6(l)(㲪"&"wòB7(l)(ɲZb&'b@8(lr)Ced8feff?ff:q(400,240):q(0,0)>τffffff?tǗd8{ab<1ɧbEݲPfe4S"<1"'{E"#uɧ"*Sb#ub#CݲPfeǗedbuɧbǗ"u"Ǘed"ɧ"ǗbbzݲPfe1᭟exN+1-.eXT-.geXT91Sa(r)6'eX6?eXNȇ2Sb(r)F1ɲZGHDzZTȟ02Sa(r)F1匄fd8Nȇ3Sb(r)F1粪TGH鲪TTȟ3Sa(r)F1܄fd8+4.S-94Sa(r)4ST6.T食5Sb(l) Ǘ GA5ǗTTO6Sb(l)粪zi鲪6Sa(l)󭁟܄fd8O7Sb(l)ɲZTziDzZT07Sa(l)󭁟匄fd8食8Sb(l) ǗedT GedTA8Ǘed矽ed ԝSa(r)&Sb(l) ԝ (Sa(r)& (Sb(l)ǻi&XkǻehCXg.f=waHXb=wc)bIj'BGdfޟff?ff:q(400,240):q(0,0)>τffffff?'TheoKhandednessforeachorientedordouble-sidedpGositionisshownwithacharactersetinparentheses.'EachKcharacterintheoptionalargumentBONDLISTspGeci esaninner(endocyclic)doublebondas'shownUUinT*able9.1. 'TheuargumentSUBSLISTuisemployedtospGecifyeachsubstituentwithaloGcantnumbGerandabond'moGdi ershowninT*able2.2,I|inwhichnisanarabicnumeralbGetween1and8.Sibstitutionon9(4a'pGosition)UUor10(8aposition)canbeassignedinthesameway*.t'Example: \quinolinev{2==CN}?\qquadKβ67D ObM'68BFUJIT*AUUShinsaku:qXMTU>'ExX'fe>|2<=GcL΍?T*ableUU9.1:qArgumentBONDLISTforcommandsnquinolinevandothersR'韻L͉ffrͤfdCharacterPqPrintedUUstructure  ffLCharacter4PrintedUUstructureffr͡noneUUorr=cdecaheteroUU(right-handed)͟ ffLl$decaheteroUU(left-handed) HUUor[]=cfullyUUsaturatedform ffa=c1,2-doubleUUbGond10^ ffLb$2,3-doubleUUbGondc=c4,3-doubleUUbGond10^ ffLd$4,4a-doubleUUbGonde=c4a,5-doubleUUbGond,0] ffLf$5,6-doubleUUbGondg=c6,7-doubleUUbGond10^ ffLh$7,8-doubleUUbGondi=c8,8a-doubleUUbGond,0] ffLj$1,8a-doubleUUbGondk=c4a,8a-doubleUUbGond'0\ ffA=caromaticUUcircle6 ffLB$aromaticUUcirclefn+g=cplusUUatthen-nitrogenatom(n=1to10)ffr͎ .8 \isoquinolinev{1==CN}\qquad \quinoxalinev{2==CH$_{3}$;3==CH$_{3}$}?\par \quinazolinev{2==CH$_{3}$;4==CH$_{3}$}\qquad \cinnolinev{4==Cl;3==Cl}?\qquad \pteridinev{2==F}ET'proGduceUUthefollowingstructures:gOdͽbhgɧbr4[ݲPfeaM"hg"S͡"P3џɧ"WMbP3џbPݲPfe?edbF3џɧb?"F3џ"5ed".ɧ"5b.b-ݲPfedͽbdbaK\"d="4W\b1拟=b4Wɘ"1拟("Lşfe^4 exNgòBCNrgɲZ"tg'"edb>ǎYbݲ<fe"ğ"ed"ߋɧ"bߋbW֟ݲPfeq*edbՋɧbq*"Ջ"q*ed"WLɧ"q*bWLb$ݲPfe>ɘb>ɘb>\"N="׎\b=Ÿ=b׎ɘ"=Ÿ(" fe%0N@CNqed8fe&֟bɧbtݲPfe&֟"ڟP"o&"kɧ"o&bkYPbkYݲPfeZs edbaɧbZs "a"Ps ed"IY.ɧ"Ps bIY.bI%ݲPfe&֟b&b&֟e"&e"Op\bM?=bOpɘ"M?("h ޟfey"exNy"NڟòBCH3ɲZ"֟'"ڟ޲CH3㲪b֟bZ|dͽbhgɧbr4[ٲ@feaM"d֫"S͡"P3џɧ"WMbP3џbPݲPfe?edbF3џɧb?"F3џ"5ed".ɧ"5b.b-ݲPfedͽbdbaK\"as\"4W\b1拟=b4Wɘ"1拟("Lşfe^4 exNnNgòBCH3rgɲZ"tg'"^4 CH3a}؄8feϟbǟb6=ݲ<feO"io"σ"5ɧ"Ob5bݲPfe՟edb5ɧb՟"5"՟ed"ɧ"՟bbşݲPfeϟbǟb-\"="9\bm=b9ɘ"m("صfe5exNǟ0N5Cl_؄8fe iClio㲪bib&֟bɧbtٲ@fe|ȟ"@֫"o&"kɧ"rȟbkbkYݲPfe]baɧb]"aP"L"IY.ɧ"LbI%PbI%ݲPfe&֟b&b}@d\"}@\"LebL֟ebL"L֟"h ޟfey"exN&NWYfNWYfexNڟòBFɲZ"֟'" 'Themmacro\quinolineviisusedtodrawquinolinederivqativesofinverseverticaltypGe(hetarom.sty). 'MacrosfordepictingotherfusedheteroGcyclesarealsode ned. Theformatsofthesecommandsareas'follows:\p \quinolinevi[BONDLIST]{SUBSLIST} \isoquinolinevi[BONDLIST]{SUBSLIST} \quinazolinevi[BONDLIST]{SUBSLIST} \cinnolinevi[BONDLIST]{SUBSLIST} \pteridinevi[BONDLIST]{SUBSLIST}ET'LoGcant$numbers$fordesignatingsubstitutionpositionsalongwithbonddescriptorsarerepresentedby'theUUfollowingdiagram:EObM'CHAPTERUU9.HETEROCYCLESWITHFUSEDSIX-MEMBEREDRINGSg69'fe>|2 {tBddDןedbk^ɧbu+ݲPfeg"kP"ZDןed"S*ɧ"VɟbRşPbRǟݲPfeBedbI*ɧbB"I*"8ed"0=ɧ"8b0=b0 ݲPfege"g e"dsɘbgx?(b7wɘ"4ݳ("7w\b4ݳ=bOfea+1Na+11(lr)d؄ ,fe^2(r)u^㲪bw^b^òB3(r)u^ɲZ"w^'"a+14(lr)ded8feh͟òB6(l)&=ɲZb$ 'bh͟޲7(l)&=㲪"$ ">u8(lr)A؄8fe>u5(lr)A響ed8fegff?ff:q(400,240) :q(0,0)>τffffff?qtrBd6edb=ܟɧbGݲPfe:& "=P",ed"% ɧ")%b%XPb%XݲPferBedb ɧbrB" " rBed"Xdɧ" rBbXdb%2ݲPfe3XN-r1.*.:1Sa(r)8rҟT8rTPs22Sb(r)Gܟ粪TH,鲪TVsJ2Sa(r)Gܟ܄fd8Ps23Sb(r)GܟɲZH,DzZVsJ03Sa(r)Gܟ匄fd8-r40edT/redT:4Sa(r)6ed7Ned^6Sb(l)XdɲZT%DzZTٻ06Sa(l)X,匄fd8^7Sb(l)Xd粪%鲪ٻ7Sa(l)X,܄fd8N8Sb(l)rB >8rBTTN5Sb(l)rBedT >edT쟯5rBeded HSa(r)'\Sb(l) H (Sa(r)'\ (Sb(l)rfe(rXkrfi8f1Xg6h?"cJNXb?"a(d+ jgȉff?ff:q(400,240) :q(0,0)>τffffff?IՍ'Example:Kō \quinolinevi{2==CN}?\qquad \isoquinolinevi{1==CN}\qquad \quinazolinevi{2==CH$_{3}$;4==CH$_{3}$}\par \cinnolinevi{4==Cl;3==Cl}?\qquad \pteridinevi{2==F}'proGduceUUthefollowingstructures:a>썍aMedbhgɧbr4[ݲPfedͽ"hP"WMed"P3џɧ"S͡bPPbPݲPfe?edbF3џɧb?"F3џ"5ed".ɧ"5b.b-ݲPfedͽe"de"aKɘbd(b4Wɘ"1拟("4W\b1拟=bLşfe^4 NgCNrg㲪btgbedbğɧbٲ@fe">֫"ed"ߋɧ"bߋbW֟ݲPfeq*edbՋɧbq*"Ջ"q*ed"WLɧ"q*bWLb$ݲPfe>\">\">ɘbN(b׎ɘ"=Ÿ("׎\b=Ÿ=b fe%N@CNq؄8fe|ȟedb@ǎYbtݲ<fe&֟"ڟP"rȟed"kɧ"o&bkYPbkYݲPfeZs edbaɧbZs "a"Ps ed"IY.ɧ"Ps bIY.bI%ݲPfe&֟e"&e"}@dɘb}@ɘbOpɘ"M?("Op\bM?=bh ޟfe&0Ny"NڟCH3㲪b֟by"CH3|sed8feY`Nedbh~ɧb5Lٲ@feή"֟"Ned"4Ÿɧ"ΒbPbݲPfeedb4Ÿɧb"4Ÿ"{ed"tɧ"{btbsԟݲPfeή"֟"<ɘb(bzHɘ"w|("zH\bw|=bfe֟N4N4Clned8fehòBClh~ɲZ"h'"6ןedb:?ǎYbGݲ<fe:%"=P",ןed"%ɧ")%ɟb%XşPb%XǟݲPfe)bɧb)"-P" "X=ɧ" b% Pb% ݲPfe:%e":& e"7?sɘb7?ɘb "" ebeb" feD& 0N31NXuNXuexNTFG㲪bIbN'9.1.2&gCommandsforGeneralUseuT'Such commandsas\quinolinev(forspGeci eduse)arebasedonthemacro\decaheterov,Rwhichis'generallyUUusedtodrawsix-six-fusedheteroGcyclesofverticaltypGe(hetarom.sty). \decaheterov[BONDLIST]{ATOMLIST}{SUBSLIST}'LoGcantXBnumbersXBfordesignatingsubstitutionpositionsaswellascharactersforsettingdoublebGondsare'shownUUinthefollowingdiagram:m?AtAdxbb\ٲ ,fex""\"4"\b4b(Zٲ ,febb"""x"bxbٲ ,fe[ğex1023[ğ4392010(5w6w07(ex8B%1ŨeXTŨ~eXTя1Sa(r)B>eXBVeXB2Sb(r)T2Dl2DB02Sa(r)T匄fd (B3Sb(r)T2Tl2TB3Sa(r)T܄fd (B%4ŨŨ~я4Sa(r)B>TBVTc5Sb(l)tڟtŸ[X5TTuƟ6Sb(l)'ğ2'2qW6Sa(l)'܄fd (uƟ7Sb(l)'ğ2DT'2DTqW07Sa(l)'匄fd (c8Sb(l)tڟeXTtŸeXT[X8eXeXA9(Z ,feA柹10(ZƲN ,feNSa(r)ȟSb(l)N (Sa(r)ȟ (Sb(l)AҟiAXkAҟehZXgfuauXbuc`j^dff?ff:q(400,240):q(0,0)>τffffff?F0mObM'70BFUJIT*AUUShinsaku:qXMTU>'ExX'fe>|2 'TheoKhandednessforeachorientedordouble-sidedpGositionisshownwithacharactersetinparentheses. 'TheoptionalargumentBONDLISTisusedtospGecifyabondpatternasshowninT*able9.1.Notethat'theUUdefaultstructureisthefullyunsaturatedone. <ҍ 'ThetargumentA*TOMLISTShasasimilarformatforpGositionsofn=1to8.#Ahetero-atomonthe'4a-pGosition;isdesignatedtobe4a==N;or9==N;andahetero-atomonthe8a-positionisgivenastobe'8a==NUUorff10gg==N. 'TheargumentSUBSLISTforthismacrotakesageneralformat,pinwhichthemoGdi erslistedinT*able'2.2UUareused.qNotethat9and10shouldbGeusedfordesignating4aand8apositions.v'Example:H'\decaheterov[H]{7==O}{6D==O;9A==H;{{10}A}==CH=CH$_{2}$}'\decaheterov[H]{5==O}{9==OH;{{10}}==OH}'\decaheterov[ch]{1==O}{9A==\lmoiety{HOCH$_{2}$};{{10}A}==H;%'4==CH$_{3}$;7==H$_{3}$C}v'proGduceUUthefollowingstructures:cosedbzɧbݲPfes"z"ied"b(ɧ"ibb(bbUݲPfeQoJedbX(ɧbQoJ"X("GoJed"CzǎY"GoJb@Ulb@":ݲ<fe<'0O+O6:e"4 "6"4n "_oHb"Ÿ̎b"Ÿ̎b"Ÿ ̎b"Ÿ(̎b"Ÿ0̎b"Ÿ8̎b"Ÿ@̎b"ŸH̎_oCH=CH2b"Ÿ̎b"Ÿ̎b"Ÿ̎b"Ÿ̎b"Ÿ̎b"Ÿ̎b"Ÿ̎b"Ÿ̎;edbɧbݲPfe;"";ed"]ɧ";b]bݭ+ݲPfeedb]ɧbF"P"ed"ɧ"FqbymPbyoݲPfeɬٟOƷOHݭ+8feƷOHݭ+ɲZ8fem~bqkNɧb{8ݲPfejQp"qkN"\b"Y7ɧ"`QpbY7bY`ݲPfeHedbO7ɧbH"O7">ed"7֟ɧ">b7֟b6ФݲPfej \"m؟="=ɘ":L("g7ʟexOg7ʟCH3j>؄8feJòBH3|sC-֟ɲZb+'b:ԩHOCH2X,̎X,̎X, ̎X,(̎X,0̎X,8̎X,@̎X,H̎V쟹HX,̎X,̎X,̎X,̎X,̎X,̎X,̎X,̎ 'Thecommand\decaheteroviistheinverse-typGemacroof\decaheterovdescribedabove(het- 'arom.sty). \decaheterovi[BONDLIST]{ATOMLIST}{SUBSLIST}'LoGcantUnumbersU(1{10)fordesignatingsubstitutionpositionsandbonddescriptors(a{f)forsettingdouble 'bGondsUUarerepresentedbythefollowingdiagram:o柍AtAdxbb\ٲ ,fex""\"4"\b4b(Zٲ ,febb"""x"bxbٲ ,fe[ğex4032[ğ1210309(8w7w06(ex5B%1ŨŨ~я1Sa(r)B>TBVTB2Sb(r)T2Tl2TB2Sa(r)T܄fd (B3Sb(r)T2Dl2DB03Sa(r)T匄fd (B%4ŨeXTŨ~eXTя4Sa(r)B>eXBVeXuƟ6Sb(l)'ğ2DT'2DTqW06Sa(l)'匄fd (uƟ7Sb(l)'ğ2'2qW7Sa(l)'܄fd (c8Sb(l)tڟtŸ[X8TTc5Sb(l)tڟeXTtŸeXT[X5eXeXA10(Z ,feA柹9(ZƲN ,feNSa(r)ȟSb(l)N (Sa(r)ȟ (Sb(l)AҟeAXkAҟifZXg?fhucuXbua^d`jff?ff:q(400,240):q(0,0)>τffffff?'TheoKhandednessforeachorientedordouble-sidedpGositionisshownwithacharactersetinparentheses.'TheUUargumentsaregiveninthesamewayasin\decaheterov.v'Example:'\decaheterovi[H]{7==O}{6D==O;9A==H;{{10}A}==CH=CH$_{2}$}'\decaheterovi[H]{5==O}{9==OH;{{10}}==OH}'\decaheterovi[ch]{1==O}{9A==\lmoiety{HOCH$_{2}$};{{10}A}==H;%'4==CH$_{3}$;7==H$_{3}$C}v'proGduceUUthefollowingstructures:GMObM'CHAPTERUU9.HETEROCYCLESWITHFUSEDSIX-MEMBEREDRINGSg71'fe>|2 usedbzɧbݲPfes"z"ied"b(ɧ"ibb(bbUݲPfeQoJedbX(ɧbQoJ"X("GoJed"@Ulɧ"GoJbCz֫b@":ٲ@fe<'O+òBO6:$b4 b6˘b4neb_oCH=CH2b"Ÿ̎b"Ÿ̎b"Ÿ ̎b"Ÿ(̎b"Ÿ0̎b"Ÿ8̎b"Ÿ@̎b"ŸH̎_oHb"Ÿ̎b"Ÿ̎b"Ÿ̎b"Ÿ̎b"Ÿ̎b"Ÿ̎b"Ÿ̎b"Ÿ̎;edbɧbݲPfe;"";ed"]ɧ";b]bݭ+ݲPfeFb]ɧb"]"Fq"ɧ"bbyoݲPfeɬٟexOƷOHݭ+8feƷOHݭ+ɲZ8fejQpedbqkNɧb{8ݲPfem~"qP"`Qped"Y7ɧ"\bbY^PbY`ݲPfeHedbO7ɧbH"O7">ed"7֟ɧ">b7֟b6ФݲPfej ɘbm؟(b=\b:L=bg7ʟOg7ʟCH3j>ed8feJ޲H3|sC-֟㲪"+"VHX,̎X,̎X, ̎X,(̎X,0̎X,8̎X,@̎X,H̎:ԩHOCH2X,̎X,̎X,̎X,̎X,̎X,̎X,̎X,̎)ɍ'9.2" DrawingffHorizontalFformsv'9.2.1&gCommandsforSp`eci edUseB'ThekhorizontalcounterpartsofthecommandsofverticaltypGe(\quinolinev,0etc)arede nedsimilarly 'inUUthestyle le,hetaromh.sty*.̍ \quinolineh[BONDLIST]{SUBSLIST} \isoquinolineh[BONDLIST]{SUBSLIST} \quinoxalineh[BONDLIST]{SUBSLIST} \quinazolineh[BONDLIST]{SUBSLIST} \cinnolineh[BONDLIST]{SUBSLIST} \pteridineh[BONDLIST]{SUBSLIST}Y'LoGcantnumbers(1{10)fordesignatingsubstitutionpositionsandbonddescriptors(a{k)arefoundin'theUUfollowingdiagram:s%tCşdF"5HջNfdPfVTb TF"5TH'TfVb 'NKЄfdPCş2|H fV2|Tb TCş2|TH[qTfV2|b [qNfdPIoeI[b"e$T`Uџe$Tb"`UџG TITP_ĘfdB;ܟhN$zf1(l)51fd (A2(lr)HTFkTh #䢲3(r)b c<[| sf4(r)lV1fd8| sL"5(r)lVefd8h #fP6(r)b LZTc<[LZTAfP7(lr)HLZGUmLZ$zL"8(l)5efd8ff?ff:q(400,800):q(0,0)>τffffff?tǗd.ջfdP5aӟT1ݟT.T'T5aӟ1ݟ'KЄfdPǗ2| 5aӟ2|T1ݟ TǗ2|T[qT5aӟ2|1ݟ[qfdPGhNiu|1Sb(l)Nj1bc1b1Sa(l)Nj˔"c˔"A`2Sb(l)b]b fI䢲2Sa(lr)[8fe?`3Sb(r)1ݟ"3 "/՟䢲3Sa(r)0᫟8feKE|4Sb(r);aӟ"=bˍ"KE4Sa(r);aӟb=b1bKE85Sb(r);aӟ2|"=bI"KE25Sa(r);aӟ2|b=beb?L6Sb(r)1ݟLZb3 b/՟fP6Sa(r)0᫟L8feAL7Sb(l)LZ"]" fIfP7Sa(lr)[L8feiu88Sb(l)Ǘ2|bgIb28Sa(l)Ǘ2|"ge"@O2D91ݟKЄfd8a2D10UKЄfd8k'2\i$ߟ2(k8/2\e8/2f$ߟ2g2hla$ߟ8b8/lc8/˼d.˼jfޟff?ff:q(400,800):q(0,0)>τffffff? \'TheoKhandednessforeachorientedordouble-sidedpGositionisshownwithacharactersetinparentheses.'TheUUoptionalargumentBONDLISTspGeci esdoublebondstobetypeset,asshowninT*able9.1.Y'Example: \quinolineh{2==CN}?\qquad \isoquinolineh{1==CN}\qquad \quinoxalineh{2==CH$_{3}$;3==CH$_{3}$}?\par \quinazolineh{2==CH$_{3}$;4==CH$_{3}$}\qquad \cinnolineh{4==Cl;3==Cl}?\qquad \pteridineh{2==F}Y'proGduceUUthefollowingstructures:HdObM'72BFUJIT*AUUShinsaku:qXMTU>'ExX'fe>|2 AcCf韨ջIf韟fdPa/T]g9TAcTCf'Ta/]g9'IfKЄfdP?2|Cf a/2|T]g9 T?2|TCf[qTa/2|]g9[qIffdPD=eE]럯e$T[e$T][CM7TE#TLĘfd= hNτffffff?qtrBdrB88fdP4T2ջTrBT8'T42'8KЄfdPrB2|8 7 ~2|T2 TrB2|T8[qT7 ~2|2[q8fdP7 fhNL|1Sb(r)@ 1"@ 1"L1Sa(r)@ ˔b@ ˔b@`2Sb(r)2"4"0䢲2Sa(r)2V8fe쟗`3Sb(l)8bb 䢲3Sa(lr)8fe |4Sb(l) rBbrˍbY4Sa(l) rB"r1"L6Sb(l)8LZ"" fP6Sa(lr)L8fe@L7Sb(r)2LZb4b0fP7Sa(r)2VL8feL88Sb(r)= ~2|"? I"L28Sa(r)= ~2|b? eb 85Sb(l) rB2|brIbY25Sa(l) rB2|"re"Br2D102KЄfd8 ş2D9KЄfd8ҟ2\i&r2(k:rڟ2\e:rڟ2f&r2g^2h2Bla&r8b:rڟlc:rڟ˼d`˼jgȉff?ff:q(400,800):q(0,0)>τffffff?#Ս'Example:[ \quinolinehi{2==CN}?\qquad \isoquinolinehi{1==CN}\qquad \quinazolinehi{2==CH$_{3}$;4==CH$_{3}$}\par \cinnolinehi{4==Cl;3==Cl}?\qquad \pteridinehi{2==F}Iz[ObM'CHAPTERUU9.HETEROCYCLESWITHFUSEDSIX-MEMBEREDRINGSg73'fe>|2 'proGduceUUthefollowingstructures:w荍?Cf韨If韟fdP_MT]g9ջT?TCf'T_M]g9'IfKЄfdP?2|Cf a/2|T]g9 T?2|TCf[qTa/2|]g9[qIffdP\埬eT[͙TCM7e$E#e$CM7TE#T][LĘfdahNcgQCN]g9^q*Ҿ ؾ fd@ fT$Tq*TҾ 'T fp'ؾ KЄfdPq*2|Ҿ  f2|Tp Tq*2|TҾ [qT f2|p[qؾ fdP"e$T֟TҤne$qZe$ҤnTqZT" 6WğĘfddN؟fCN f1fd8Zs \Yhfd@z؟TxRջTZs T^'Tz؟xR'dKЄfdPZs 2|^ } H2|TxR TZs 2|T^[qT} H2|xR[qdfdPwYeTw&T^Pe$^ٜ^PT`s<Txw gYĘfd`sAN} 0hN~jCH3xRy󢟜7BfCH3Lrԟ1fd8y䟯gڟgڟfd@NTd6T䟹Tgڟ'TNh*'gڟKЄfdP2|gڟ  2|Th* T2|Tgڟ[qT 2|h*[qgڟfdP֟eTΊTN(e$e$N(TTܟ~ĘfdhNhNkgqfClw1fd8gClgڟT4TrX"!fd@4矫T2aջTrT'T4矽2a'KЄfdP؋2l w42lT2a wT؋2T[T422a[fdP1Y eT1%T_e$ث%e$TX T1Y $1% !XĘfdrPN7 ?hN7 ?$N2$N8yF2a3򱟜㓍'9.2.2&gCommandsforGeneralUseuT'Themacro\decaheteroh(carom.sty)isthehorizotalcounterpartof\decaheterov.WTheformatand 'theassignmentofBONDLISTŧandSUBSLISToftheformermacroarethesameasthoseofthelatter'describGedUUabove(seeT*ables2.2and9.1).A \decaheteroh[BONDLIST]{ATOMLIST}{SUBSLIST}'LoGcantnumbersfordesignatingsubstitutionpositionsandbonddescriptorsfortypesettingdoublebonds 'areUUrepresentedbythefollowingdiagram:AtAdj6fd 0uzTB.6TTjSJTuzB.SJKЄfd 02ljuz2lTB.T2TjTuz2B.fd 0Aşh1㟡2Ǝ蟡3ҟh4Ǝ910ҟ$5ƎLj6Lj7Aş$8㌟|1Sb(l)A1bAz1bqş1Sa(l)A˔"Az˔"}T`2Sb(l)(,֬b(b`䢲2Sa(lr)[r΄ (fe׏,`3Sb(r)͏֬"͏,"ǎ쟎䢲3Sa(r)[Ÿ΄ ,fe\|4Sb(r)1"1"\4Sa(r)˔b˔b\85Sb(r)e"e"\25Sa(r)PbPb׏,L6Sb(r)͏Lfb͏,LfbǎfP6Sa(r)[ŸL ,fe}XL7Sb(l)(,Lf"(Lf"`fP7Sa(lr)[rL (fe㌟88Sb(l)AebAzebqş28Sa(l)AP"AzP"Bf2D9̏KЄfd ,02D10lKЄfd ,>2\iA2(kBF2\eBF2fA2gʟ2hlaA8bBFlcBF˼d̟˼jff?ff:q(400,800):q(0,0)>τffffff?\n'TheoKhandednessforeachorientedordouble-sidedpGositionisshownwithacharactersetinparentheses.'TheUUoptionalargumentBONDLISTcontainsacharacherstringselectedfromT*able9.1.!'Example:A'\decaheteroh[H]{7==O}{6D==O;9A==H;{{10}A}==CH$_{2}$=CH}'\decaheteroh[H]{5==O}{9==OH;{{10}}==HO}'\decaheteroh[ch]{1==O}{9A==CH$_{2}$OH;{{10}A}==H;%'4==CH$_{3}$;7==CH$_{3}$}J ObM'74BFUJIT*AUUShinsaku:qXMTU>'ExX'fe>|2 'proGduceUUthefollowingstructures:󧍍QoJU@[@fdPt ToTQoJTU@'Tt o'[@KЄfdPQoJ2|U@ t 2|To TQoJ2|TSUП[qTt 2|o[q_Pfd@W(bLjOufPOpoƟTqTm"(To r(Tp2DHoV*̎qV2̎sV:̎uVB̎wVJ̎yVR̎{VZ̎}Vb̎"Ss2DCH2|s=CH[Uڟ̎YUҟ̎WUʟ̎UUŸ̎SU̎QU̎OU̎MU̎uufdP`TşTTu'T`ş'uKЄfdP2|u K2lTş wT2|Tu[qTK2ş[ufdP`$O72DOHşKЄfd82DHO=KЄfd8J$LjջRjfdPjTfjTJ$TLj'Tjfj'RjKЄfdPH2|Lj j2|Tfj TH2|TLj[qTj2|fj[qRjfdPfe$Tde$TLPTNTFVhOkbfCH3p1fd8EjvfPCH3L꬟LZK\LZvl2DCH2|sOHf̎h̎j̎l̎n̎p̎rğ̎t̟̎;772DHRD̎P<̎N4̎L,̎J$̎H̎F̎D ̎ 'TheCmacro\decaheterohi(carom.sty)istheinversecounterpartof\decaheteroh.kTheformatand 'theassignmentofBONDLISTandSUBSLISToftheformermacroarethesameasthelatter(seeT*ables'2.2UUand9.1). \decaheterohi[BONDLIST]{ATOMLIST}{SUBSLIST}'LoGcantgnumbersgfordesignatingsubstitutionpositionsandbonddescriptorsforsettingdoublebondsare'representedUUbythefollowingdiagram:󧍍AtAdj6fd 0uzTB.6TTjSJTuzB.SJKЄfd 02ljuz2lTB.T2TjTuz2B.fd 0Aşh4㟡3Ǝ蟡2ҟh1Ǝ109ҟ$8ƎLj7Lj6Aş$5\|1Sb(r)1"1"\1Sa(r)˔b˔b׏,`2Sb(r)͏֬"͏,"ǎ쟎䢲2Sa(r)[Ÿ΄ ,fe}T`3Sb(l)(,֬b(b`䢲3Sa(lr)[r΄ (fe㌟|4Sb(l)A1bAz1bqş4Sa(l)A˔"Az˔"}XL6Sb(l)(,Lf"(Lf"`fP6Sa(lr)[rL (fe׏,L7Sb(r)͏Lfb͏,LfbǎfP7Sa(r)[ŸL ,fe\88Sb(r)e"e"\28Sa(r)PbPb㌟85Sb(l)AebAzebqş25Sa(l)AP"AzP"Bf2D10̏KЄfd ,12D9lKЄfd ,>2\iA2(kBF2\eBF2fA2gʟ2hlaA8bBFlcBF˼d̟˼jff?ff:q(400,800):q(0,0)>τffffff?!-'Example:'\decaheterohi[H]{7==O}{6D==O;9A==H;{{10}A}==CH=CH$_{2}$}'\decaheterohi[H]{5==O}{9==HO;{{10}}==OH}'\decaheterohi[ch]{1==O}{9A==\lmoiety{HOCH$_{2}$};{{10}A}==H;%'4==CH$_{3}$;7==CH$_{3}$}'proGduceUUthefollowingstructures:󧍍QoJU@[@fdPt ToTQoJTU@'Tt o'[@KЄfdPQoJ2|U@ t 2|To TQoJ2|TU@[qTt 2|r#[q[@fd@lLjON fPOU SպW(VUğ(p2DCH=CH2oV*̎qV2̎sV:̎uVB̎wVJ̎yVR̎{VZ̎}Vb̎D͟2DH[Uڟ̎YUҟ̎WUʟ̎UUŸ̎SU̎QU̎OU̎MU̎uufdP`TşTTu'T`ş'uKЄfdP,2lu w`2|Tş T,2Tu[T`2|ş[qufdPy$O72DOHşKЄfd82DHO=KЄfd8HLjRjfdPhQTfjջTHTLj'ThQfj'RjKЄfdPH2|Lj j2|Tfj TH2|TLj[qTj2|fj[qRjfdPLPe$N䟬e$fdj؟hO%4ꟳfCH3:|1fd8lkfPCH3fjLZTgJLZTvl2DHf̎h̎j̎l̎n̎p̎rğ̎t̟̎ :2DHOCH2RD̎P<̎N4̎L,̎J$̎H̎F̎D ̎KߠObM2(ɍ'UChapter 102'THetero cycles T{withFusedSix-and'Fiv8e-Memb ered T{Rings:'10.1*'DrawingffVferticalForms ?'10.1.1-'CommandsforSp`eci edUsex'XMTU>'ExXeinvolvesmacrosfordrawingrepresentativefusedN-heteroGcyclesthatconsistofasix-anda ' ve-membGeredUUring.qThesehaveUUthefollowingformats(hetarom.sty).zЍ \indolev[BONDLIST]{SUBSLIST} \isoindolev[BONDLIST]{SUBSLIST} \purinev[BONDLIST]{SUBSLIST}\'MacrosffordrawingfusedN,O-heteroGcyclesarealsoavqailable(hetarom.sty).Theyarethesameformats'ofUUarguments. \benzofuranev[BONDLIST]{SUBSLIST} \isobenzofuranev[BONDLIST]{SUBSLIST} \benzoxazolev[BONDLIST]{SUBSLIST}\'TheUUloGcantnumbGeringiscommoninthesecommandsasshowninthefollowingdiagram:on'%tCşdv-ݲPfeio"mτffffff?tǗdEݲPfe8{a"τffffff?4I'TheoKhandednessforeachorientedordouble-sidedpGositionisshownwithacharactersetinparentheses.'TheUUoptionalargumentBONDLISTspGeci esedgeswithadoublebond(T*able10.1).  'TheV!argumentSUBSLISTUisusedtospGecifyeachsubstituentwithaloGcantnumbGerandabondmodi er'shownbinT*able2.2,einwhichnisanarabicnumeralbGetween1and7.Sibstitutionon8(3apGosition)or'9UU(7apGosition)canbeassignedinthesameway*.\'Example:K75LObM'76CFUJIT*AUUShinsaku:XMTU>'ExX'fe>|20=GoL΍D߬T*ableUU10.1:qArgumentBONDLISTforcommandsnindolevandothersL3"L͉ffY[fdCharacterTBPrintedUUstructureW| ff1Character+PrintedUUstructureffY[noneUUorr=caromaticUUsix-membGeredring͟ ff1HUUor[]$fullyUUsaturatedform a=c1,2-doubleUUbGond:)C ff1b$2,3-doubleUUbGondc=c3,3a-doubleUUbGond5)B ff1d$4,3a-doubleUUbGonde=c4,5-doubleUUbGond:)C ff1f$5,6-doubleUUbGondg=c6,7-doubleUUbGond:)C ff1h$7,7a-doubleUUbGondi=c1,7a-doubleUUbGond5)B ff1j$3a,4a-doubleUUbGondA=caromaticUUcircle(six-membGeredring)B=caromaticUUcircle( ve-membGeredUUring)fn+g=cplusUUatthen-nitrogenatom(n=1to9)ffY[jS \indolev{1==H;2==COOH}\qquad \isoindolev{2==H;1==CN;3==CN}\qquad \purinev{3==H}jS'proGduceUUthefollowingstructures:b]zsݲPfefxg"jEkP"UxKbQGPbQIݲPfeQ{匄fd"3@ĝedbG{ɧb@ĝ"G{"6ĝed"/ɧ"6ĝb/b/wݲPfeN^ofe6+ɘ"35("6+\b35=bp+fe_޳N_޳Hb'؄ ,fekCOOHt7㲪bvgbٲ@fe;" ֫";b]bݭ+ݲPfe]匄fd"3edb]ɧb"]"ed"ɧ"bbyoݲPfe-72ffd,ɘ"(",\b=b`\bӟ=bzqNQH%bMbCN ؄8fe MòBCNɲZ"I'"ɟݲ<fe~|+"I/P"m|bi Pbi ݲPfei?匄fdxXaedb_?ɧb\Ho"`sP"Naed"K.ǎY"KHSbG{OPbG{Qݲ<fefb3feN.şɘ"N.ɘ"KHSebKH+eb~|+e"~|Se"wwN|S0NC*0NUN3òBHK"/K"}'Example: \benzofuranev{2==COOH}\qquad \isobenzofuranev{1==Ph;3==Ph}\qquad \benzoxazolev{2==CH$_{3}$;5==HO}jS'proGduceUUthefollowingstructures:sݲPfefxg"jEkP"UxKbQGPbQIݲPfeQ{匄fd"3@ĝedbG{ɧb@ĝ"G{"6ĝed"/ɧ"6ĝb/b/wݲPfeN^ofe6+ɘ"35("6+\b35=bp+fe_޳OkCOOHt7㲪bvgbٲ@fe;" ֫";b]bݭ+ݲPfe]匄fd"3edb]ɧb"]"ed"ɧ"bbyoݲPfe-72ffd,ɘ"(",\b=b`\bӟ=bzqOPh ؄8fe MòBPhɲZ"I'"ɟݲ<fe~|+"I/P"m|bi Pbi ݲPfei?匄fdxXaedb_?ɧbXa"_?"Naed"Gɧ"NabGbG{QݲPfefb3feN.şɘ"K("N.ş\bK=b ffewwO|S0N/CH3㲪b+b+g0òBHO=ɲZb;S'b 'MacrosfordrawingfusedN-heteroGcyclesofinverseverticaltypGehavethefollowingformats(het- 'arom.sty). \indolevi[BONDLIST]{SUBSLIST} \isoindolevi[BONDLIST]{SUBSLIST} \purinevi[BONDLIST]{SUBSLIST}'Macros@gfordrawingfusedN,O-heteroGcyclesofinverseverticaltypGehavethefollowingformats.jTheyare'alsoUUcontainedinthestyle le`hetarom.sty'.MɠObM'CHAPTERUU10.HETEROCYCLESWITHFUSEDSIX-ANDFIVE-MEMBEREDRINGS*77'fe>|2  \benzofuranevi[BONDLIST]{SUBSLIST} \isobenzofuranevi[BONDLIST]{SUBSLIST} \benzoxazolevi[BONDLIST]{SUBSLIST}荑'They[arethecounterpartsofthecommandswithoutsux`i'describGedabove. The[locant[numbering[is'commonUUinthesecommandsasshowninthefollowingdiagram:r%tCşdiobm _ɧbv-ݲPfeTqݲPfeXos"Tգɧ"Tգ܄fd"3CşedbJգɧbCş"Jգ"9şed"2ɧ"9şb2b2nݲPfeQUfe9")ɘ"6]("9")\b6]=bsSfeb۟exNb۟1(lr)eOeX ,fe òB2(r)w _ɲZ"y '" ޲3(r)w _㲪by b@4(lr)C؄8few5(l)(㲪"&"wòB6(l)(ɲZb&'b@7(lr)Ced8feff?ff:q(400,240):q(0,0)>τffffff?tǗd8{ab<1ɧbEݲPfe#CݲPfe'{E"#uɧ"#u܄fd"3ǗedbuɧbǗ"u"Ǘed"ɧ"ǗbbzݲPfe1᭟exN+1-.eXT-.geXT91Sa(r)6'eX6?eXNȇ2Sb(r)F1ɲZGHDzZTȟ02Sa(r)F1匄fd8Nȇ3Sb(r)F1粪TGH鲪TTȟ3Sa(r)F1܄fd8食4Sb(l) Ǘ GA4Sa(r)ǗTTO5Sb(l)粪zi鲪5Sa(l)󭁟܄fd8O6Sb(l)ɲZTziDzZT06Sa(l)󭁟匄fd8食7Sb(l) ǗedT GedTA7Ǘed矽ed ϟ8#C8fe ϟ9#CɲZ8feǻh&Xjǻdog.aXfSe=waHXb3wc)ifޟff?ff:q(400,240):q(0,0)>τffffff?'TheoKhandednessforeachorientedordouble-sidedpGositionisshownwithacharactersetinparentheses.'TheUUoptionalargumentBONDLISTisusedinausualway(T*able10.1).荑'Example:5 \indolevi{1==H;2==COOH}\qquad \isoindolevi{2==H;1==CN;3==CN}\qquad \purinevi{3==H}'proGduceUUthefollowingstructures:f\fxgbj7ɧbsݲPfeQIݲPfeUxK"Q{ɧ"Q{܄fd"3@ĝedbG{ɧb@ĝ"G{"6ĝed"/ɧ"6ĝb/b/wݲPfeN^ofe6+ɘ"35("6+\b35=bp+fe_޳exN_޳Hb'eX ,fekòBCOOHt7ɲZ"vg'";edb ǎYbݲ<feݭ+ݲPfe;ed"]ɧ"]܄fd"3edb]ɧb"]"ed"ɧ"bbyoݲPfe-7ڙfd,\b=b,ɘ"("`ɘ"ӟ("zq0NQòBH%K"MK"CN ed8fe MCN㲪bIb~|+bɧbɟٲ@fei ݲPfem|"i?ɧ"i?܄fdx\Hob_?ɧbXa"_?"KHS"Gɧ"NabK.֫bG{Qٲ@fefb3feKHS"KH+"N.ş\bN.\b~|+b~|SbwwexN|SNUexNC*N3Hb/b胍'Example:5 \benzofuranevi{2==COOH}\qquad \isobenzofuranevi{1==Ph;3==Ph}\qquad \benzoxazolevi{2==CH$_{3}$;5==HO}'proGduceUUthefollowingstructures:f\fxgbj7ɧbsݲPfeQIݲPfeUxK"Q{ɧ"Q{܄fd"3@ĝedbG{ɧb@ĝ"G{"6ĝed"/ɧ"6ĝb/b/wݲPfeN^ofe6+ɘ"35("6+\b35=bp+fe_޳exOkòBCOOHt7ɲZ"vg'";edb ǎYbݲ<feݭ+ݲPfe;ed"]ɧ"]܄fd"3edb]ɧb"]"ed"ɧ"bbyoݲPfe-7ڙfd,\b=b,ɘ"("`ɘ"ӟ("zq0OPh ed8fe MPh㲪bIb~|+bɧbɟٲ@fei ݲPfem|"i?ɧ"i?܄fdxXaedb_?ɧbXa"_?"Naed"Gɧ"NabGbG{QݲPfefb3feN.şɘ"K("N.ş\bK=bٲ ffewwexO|SN/òBCH3ɲZ"+'"+g0޲HO=㲪";S"N㨠ObM'78BFUJIT*AUUShinsaku:qXMTU>'ExX'fe>|2 '10.1.2-'CommandsforGeneralUse8'Macros8forspGeci edusesuchas\indolevareshort-cutcommandsbasedonageneralcommand\nonaheterov. 'SuchS ageneralcommandenablesustodrawafurthervqarietyofheteroGcycliccompounds.qIthasthefol-'lowingUUformat,thede nitionofwhichiscontainedalsoinhetarom.sty*.< \nonaheterov[BONDLIST]{ATOMLIST}{SUBSLIST}'LoGcantUUnumbersUU(1{9)andbonddescriptors(a{j)arede nedasshowninthefollowingdiagram:vG̍AtAd\ٲ ,fex""\b4b(Zٲ ,feП匄fd4bb"""x"bxbٲ ,fe[ğ1203308(ex4w05w6(739B%1ŨŨ~я1Sa(r)B>TBVTB2Sb(r)T2Tl2TB2Sa(r)T܄fd (B3Sb(r)T2Dl2DB03Sa(r)T匄fd (uƟ5Sb(l)'ğ2DT'2DTqW05Sa(l)'匄fd (uƟ6Sb(l)'ğ2'2qW6Sa(l)'܄fd (c7Sb(l)tڟtŸ[X7TTc4Sb(l)tڟeXTtŸeXT[X4Sa(r)eXeXA9(Z ,feA柹8(ZƲN ,feAҟdAXjAҟhzjexXfgupcuXbuaҟiff?ff:q(400,240):q(0,0)>τffffff? ڍ'TheoKhandednessforeachorientedordouble-sidedpGositionisshownwithacharactersetinparentheses.'TheUUoptionalargumentBONDLISTisusedtospGecifydoublebondsasshowninT*able10.1. 'The2argumentA*TOMLIST2takesausualformatwithrespGecttoheteroatomsattachedton=1to7,'e.g.,`1==Nforanitrogenatomat1-pGosition.T7Heteroatomsat3a-and7a-positionsarerepresentedasto'bGe7.3a==N7'(or8==N)foranitrogenat3a-pGosition,=67a==N(or9==N)foratanitrogenat7a-pGosition,'and]soon.VTheaugumentSUBSLISTHtakesausualformatexceptthattheloGcantnumbGers3aand7aare'replacedUUby8and9.'Example:g\nonaheterov[bjg]{1==N;3==N;5==N;7==N}{1==H;5==H;4D==O}g\nonaheterov[bjge]{1==N;5==N;7==N}%{1==H;3==C$_{6}$H$_{5}$;4==NHCH$_{3}$}g\nonaheterov[bjge]{1==S;2==N}{3==Cl}'proGduceUUthefollowingstructures:icݲ<few#"zP"f"bbUPbbUݲPfeb(匄fdxQoJedbX(ɧbTX"X\P"GoJed"CzǎY"Ced"7֟ɧ">b7֟b6ФݲPfewBٲ ffeUfe=\b:L=b=ɘ":L("g7ʟSwѦNkòBCl{kNɲZ"}k~'" 'TheUUinverseconterpart\nonaheterovihasthefollowingformat: \nonaheterovi[BONDLIST]{ATOMLIST}{SUBSLIST}'LoGcantUUnumberingUUisusuallyde nedasshowninthefollowingdiagram:O&ObM'CHAPTERUU10.HETEROCYCLESWITHFUSEDSIX-ANDFIVE-MEMBEREDRINGS)l79'fe>|2 AtAdxbb\ٲ ,fe(Zٲ ,fe\"4"П܄fd4bb"""x"bxbٲ ,fe[ğex1302309(ex7w06w5(438B%1ŨeXTŨ~eXTя1Sa(r)B>eXBVeXB2Sb(r)T2Dl2DB02Sa(r)T匄fd (B3Sb(r)T2Tl2TB3Sa(r)T܄fd (c4Sb(l)tڟtŸ[X4Sa(r)TTuƟ5Sb(l)'ğ2'2qW5Sa(l)'܄fd (uƟ6Sb(l)'ğ2DT'2DTqW06Sa(l)'匄fd (c7Sb(l)tڟeXTtŸeXTeXeXA8(Z ,feA柹9(ZƲN ,feAҟhAXjAҟdgxXfzjeuauXbucҟiff?ff:q(400,240) :q(0,0)>τffffff?!'TheoKhandednessforeachorientedordouble-sidedpGositionisshownwithacharactersetinparentheses. 'TheUUsameformatoftheoptionalargumentBONDLISTisusedasshowninT*able10.1.a'Example:āg\nonaheterovi[bjg]{1==N;3==N;5==N;7==N}{1==H;5==H;4D==O}g\nonaheterovi[bjge]{1==N;5==N;7==N}%{1==H;3==C$_{6}$H$_{5}$;4==NHCH$_{3}$}g\nonaheterovi[bjge]{1==S;2==N}{3==Cl}a'proGduceUUthefollowingstructures:jw#bzɧbٲ@febUݲPfef""b(ɧ"b(܄fdxTXbX(ɧbQoJ"X("C<"@Ulɧ"GoJbCz֫b@":ٲ@fe<؟ٲ ffe_ feC<"C"p`exN#<NNUexNed"7֟ɧ">b7֟b6ФݲPfewB ffeUfe=ɘ":L("=\b:L=bg7ʟexSwѦ0NkCl{kN㲪b}k~b+_J'10.2*'DrawingffHorizontalFformsL'10.2.1-'CommandsforSp`eci edUse'MacrosUUfordrawingN-heteroGcyclesofhorizontaltypGehavethefollowingformats(hetaromh.sty). \indoleh[BONDLIST]{SUBSLIST} \isoindoleh[BONDLIST]{SUBSLIST} \purineh[BONDLIST]{SUBSLIST}a'Macros~fordrawingN,O-heteroGcyclesareavqailablebysettingtheoptionstyle le`hetaromh.sty'.YAThey'haveUUthefollowingformats. \benzofuraneh[BONDLIST]{SUBSLIST} \isobenzofuraneh[BONDLIST]{SUBSLIST} \benzoxazoleh[BONDLIST]{SUBSLIST}a'LoGcantUUnumbersUUfordesignatingsubstitutionpositionsarerepresentedbythefollowingdiagram:PObM'80CFUJIT*AUUShinsaku:XMTU>'ExX'fe>|2 %tCşdNfdPcTb ջTcb 'NKЄfdPMՉ"3feCş2|H fV2|Tb TCş2|TH[qTfV2|b [qNfdPP_ĘfdG TITb"`UџP_dfdgUퟳhN| sf1(r)oV 1fd ,h #2(lr)b c<[A䢲3(lr)HTFkTAfP5(lr)HLZGUmLZh #fP6(lr)b LZTc<[LZT| sL"7(r)lVefd8$zL"4(l)5efd8ff?ff:q(400,800) :q(0,0)>τffffff?tǗdfdP2cT1ݟջT2c1ݟ'KЄfdP["3feǗ2| 5aӟ2|T1ݟ TǗ2|T[qT5aӟ2|1ݟ[qfdP6ahNKE|1Sb(r)>aߟ1">b1"KE1Sa(r)>aߟ˔b>b˔b?`2Sb(r)1ݟ"3 "/՟䢲2Sa(lr)0᫟8feA`3Sb(l)b]b fI䢲3Sa(lr)[8feAL5Sb(l)LZ"]" fIfP5Sa(lr)[L8fe?L6Sb(r)1ݟLZb3 b/՟fP6Sa(lr)0᫟L8feKE87Sb(r);aӟ2|"=bI"KE27Sa(r);aӟ2|b=bebiu84Sb(l)Ǘ2|bgIb24Sa(l)Ǘ2|"ge"@O2D91ݟKЄfd8a2D8UKЄfd82\d$ߟ2(j8/2\h8/2g$ߟ2f{2eOlc$ߟ8b8/la8/˼ifޟff?ff:q(400,800) :q(0,0)>τffffff?;'TheoKhandednessforeachorientedordouble-sidedpGositionisshownwithacharactersetinparentheses. 'TheUUoptionalargumentBONDLISTspGeci esdoublebondsbyusingchractersselectedfromT*able9.1.i'Example: \indoleh{1==H;2==COOH}\qquad \isoindoleh{2==H;1==CN;3==CN}\qquad \purineh{3==H}'proGduceUUthefollowingstructures:ŵKfdP`iT_㟨ջT`i_'KKЄfdPJa"3fe@ĝ2|E c^ٟ2|T_ T@ĝ2|TE[qTc^ٟ2|_[qKfdPM7ĘfdDTF͟T_+]^M7dfdd^şhNyKfHl^埰1fd ,eCOOH_㟞`E3ufd@`Tz5T`ş'uKЄfdPC"3fe2|u `2|Tş T2|Tu[qT`2|ş[qufdP-ĄfeßTƯT-w`-w\`\NݟH՟άG!T-fCN`1fd8ACNuT%Tggfd@x-TwջTx-w'cWKЄfdPb%xfeXa2|]W x-2lTw wTXa2|TZ[qTx-2w[ggfd@eĘfd\T]. TuS$u| uSeTu|T|bhN^ȖN^ȖLjN|b$NV#HZ矙άTZ{TT;'Example: \benzofuraneh{2==COOH}\qquad \isobenzofuraneh{1==Ph;3==Ph}\qquad \benzoxazoleh{2==CH$_{3}$;5==HO}'proGduceUUthefollowingstructures:ŵKfdP`iT_㟨ջT`i_'KKЄfdPJa"3fe@ĝ2|E c^ٟ2|T_ T@ĝ2|TE[qTc^ٟ2|_[qKfdPM7ĘfdDTF͟T_+]^M7dfdd^şhOeCOOH_㟞`E3ufd@`Tz5T`ş'uKЄfdPC"3fe2|u `2|Tş T2|Tu[qT`2|ş[qufdP-ĄfeßTƯT-w`-w\`\O-fPh`1fd8APhuT%Tggfd@x-TwջTx-w'cWKЄfdPb%xfeXa2|]W {b2|Tw TXa2|T]W[qT{b2|w[qcWfdPeĘfd\T^ȑTw/Yubmggdfd f|bhO^ȖN}CH3wxHV#fPHO]YLZ\b LZ 'Themacro\indolehiisusedtodrawinoGdelederivqativesofinversehorizontaltypGe(hetaromh.sty).'MacrosNfordrawingotherfusedheteroGcyclesarealsode nedinthehetaromh.sty*.Theformatofthese'commandsUUisasfollows:QObM'CHAPTERUU10.HETEROCYCLESWITHFUSEDSIX-ANDFIVE-MEMBEREDRINGS)l81'fe>|2  \indolehi[BONDLIST]{SUBSLIST} \isoindolehi[BONDLIST]{SUBSLIST} \purinehi[BONDLIST]{SUBSLIST} \benzofuranehi[BONDLIST]{SUBSLIST} \isobenzofuranehi[BONDLIST]{SUBSLIST} \benzoxazolehi[BONDLIST]{SUBSLIST}\p'LoGcantnumbersfordesignatingsubstitutionpositionsandcharactersfordescribingbondstobedoubled'areUUshowninthefollowingdiagram:n獍{tBdDwF^ջL^fdPL^KЄfdPDwTF^'T`+/"3feB2|F^ dW2|T`^a TB2|TF^[qTdW2|`^a[qL^fdPNĘfdFD_THKT`x^'Ndfd?.hN"mf1(l)4㟰1fd (?]ݟ2(lr)F^TE*Tf^y䢲3(lr)`^aaz^ɟL"4(r)jWefd8f^yfP5(lr)`^aLZTaLZT?]ݟfP6(lr)FLZEßLZ"mL"7(l)4efd8gff?ff:q(400,800):q(0,0)>τffffff?qtrBdز8ջ8fdP8KЄfdPزT8'T2V"3ferB2|8 7 ~2|T2 TrB2|T8[qT7 ~2|2[q8fdPUhN |1Sb(l)r61br1bY1Sa(l)r6˔"r˔"쟗`2Sb(l)8bb 䢲2Sa(lr)8fe@`3Sb(r)2"4"0䢲3Sa(lr)2V8feL84Sb(r)= ~2|"? I"L24Sa(r)= ~2|b? eb@L5Sb(r)2LZb4b0fP5Sa(r)2VL8fe^L6Sb(r)8LZ"" fP6Sa(lr)L8fe 87Sb(l) rB2|brIbY27Sa(l) rB2|"re"Br2D82KЄfd8 ş2D9KЄfd8^2\h&r2(i:rڟ2\d:rڟ2e&r2f2B2g2Bla&r8b4lcҟ˼igȉff?ff:q(400,800):q(0,0)>τffffff?,r='Example:{@ \indolehi{1==H;2==COOH}\qquad \isoindolehi{2==H;1==NC;3==CN}\qquad \purinehi{3==H}'proGduceUUthefollowingstructures:n獍C+ EջKfdPKKЄfdPC+ TE'T^ޱ"3fe@ĝ2|E c^ٟ2|T_ T@ĝ2|TE[qTc^ٟ2|_[qKfdPM7ĘfdDTF͟T_+]^M7dfd>DhN)*fH2e1fd (>_COOHETCCTέfd@uKЄfdPTu'T"3fe2|u `2|Tş T2|Tu[qT`2|ş[qufdP瓹Ąfe-w`ßTƯTß\TƯ\TƴNAHέάTyTTZ(fNCG1fd8ݟCNşG[.џ]WջcWfd@cWKЄfdP[.џT]W'Tvuxfe[.џ2l]W w{b2|Tw T[.џ2T]W[T{b2|y|[qcWfd@eĘfd^{$T^ Tw/Yv ^{e^VHthNtNVHt$NtLjN}H{ά{IT$'Example:{@ \benzofuranehi{2==COOH}\qquad \isobenzofuranehi{1==Ph;3==Ph}\qquad \benzoxazolehi{2==CH$_{3}$;5==OH}'proGduceUUthefollowingstructures:R6͠ObM'82BFUJIT*AUUShinsaku:qXMTU>'ExX'fe>|2 C+ EջKfdPKKЄfdPC+ TE'T^ޱ"3fe@ĝ2|E c^ٟ2|T_ T@ĝ2|TE[qTc^ٟ2|_[qKfdPM7ĘfdDTF͟T_+]^M7dfd=hO>_COOHETCCTέfd@uKЄfdPTu'T"3fe2|u `2|Tş T2|Tu[qT`2|ş[qufdP瓹Ąfe-w`ßTƯTß\TƯ\TOfPhG1fd8ݟPhşG[.џ]WջcWfd@cWKЄfdP[.џT]W'TvuxfeXa2|]W {b2|Tw TXa2|T]W[qT{b2|w[qcWfdPeĘfd\T^ȑTw/Yubmedfd fVWhOtNV#CH3]WT[T}fPOHwLZTxHLZT%'10.2.2-'CommandsforGeneralUseڍ'MacrosNforspGeci edusesuchas\indoleharebasedonageneralcommand\nonaheteroh.CThiscommand 'enableKustodrawafurthervqarietyofheteroGcycliccompounds.1oThismacrohasthefollowingformatwhich'isUUcontainedalsoinhetaromh.sty*.Lۍ \nonaheteroh[BONDLIST]{ATOMLIST}{SUBSLIST}y'TheUUloGcantnumbGeringiscommoninthesecommandsasshowninthefollowingdiagram:@AtAdfd 0uzTB.6TuzB.SJKЄfd 0[rZ4fe2ljuz2lTB.T2TjTuz2B.fd 0֟h1Ǝ蟡2㟡38A$4Lj5ƎLj6֟$7Ǝ9\|1Sb(r)1"1"\1Sa(r)˔b˔b׏,`2Sb(r)͏֬"͏,"ǎ쟎䢲2Sa(lr)[Ÿ΄ ,fe}T`3Sb(l)(,֬b(b`䢲3Sa(lr)[r΄ (fe}XL5Sb(l)(,Lf"(Lf"`fP5Sa(lr)[rL (fe׏,L6Sb(r)͏Lfb͏,LfbǎfP6Sa(lr)[ŸL ,fe\87Sb(r)e"e"\27Sa(r)PbPb㌟84Sb(l)AebAzebqş24Sa(l)AP"AzP"Bf2D9̏KЄfd ,12D8lKЄfd ,ʟ2\dA2(jBF2\hBF2gA2fz2eGflcA8bBFlaBF˼iff?ff:q(400,800):q(0,0)>τffffff?!Qэ'TheoKhandednessforeachorientedordouble-sidedpGositionisshownwithacharactersetinparentheses.'CharacterslistedinT*able10.1arealsousedtospGecifydoublebondsbysettingthemintotheoptional'argumentUUBONDLIST. 7 'The2argumentA*TOMLIST2takesausualformatwithrespGecttoheteroatomsattachedton=1to7,'e.g.,,1==NGforaanitrogenatomat1-pGosition.O!Hetero-atomsat3a-and7b-positionsarerepresentedasto'bGe7.3a==N7'(or8==N)foranitrogenat3a-pGosition,=67a==N(or9==N)foratanitrogenat7a-pGosition,'and]soon.VTheaugumentSUBSLISTHtakesausualformatexceptthattheloGcantnumbGers3aand7aare'replacedUUby8and9.y'Example:g\nonaheteroh[bjg]{1==N;3==N;5==N;7==N}{1==H;5==H;4D==O}g\nonaheteroh[bjge]{1==N;5==N;7==N}%{1==H;3==C$_{6}$H$_{5}$;4==NHCH$_{3}$}g\nonaheteroh[bjge]{1==S;2==N}{3==Cl}y'proGduceUUthefollowingstructures:SHLObM'CHAPTERUU10.HETEROCYCLESWITHFUSEDSIX-ANDFIVE-MEMBEREDRINGS)l83'fe>|2 _Pfd@qToջTqo'[@KЄfdP[xfeQoJ2|U@ q2lTo wTQoJ2|TSUП[qTq2o[_Pfd@_Pdfd f^UĘfdnV<$n" u rhNWoNWoLjNu r$NfH} 1fd ,N fPHSUПLnS"9L"OCoӘfd8Co2vfd8ufdPKTşջTKş'uKЄfdPC"3fe2|u K2lTş wT2|Tέ[qTK2ş[fd@٭dfd٭Ęfdq$z% ßT- T`hNƴLjN`$N-fH`ǟ1fd ,AC6|sH5uT%TݳL"NHCH3Gefd8Rjfd@hQTh46ThQfj'RjKЄfdPR7x"3feH2|Lj j2|Tfj TH2|TLj[qTj2|fj[qRjfdPUNdfd fUNĘfdfdLPTNTkܟhScjNEjvClLjTK7ZT 'TheUUinverseconterpart\nonaheterohiarealsoavqailablebysetting`hetaromh.sty'.qItsformatis: \nonaheterohi[BONDLIST]{ATOMLIST}{SUBSLIST}'ItsUUloGcantnumbGeringiscommonwiththenormalcounterpartasshowninthefollowingdiagram:󧍍AtAdj6fd 0KЄfd 0TjSJT[ŸZ4fe2ljuz2lTB.T2TjTuz2B.fd 0Ah1Ǝ蟡3㟡29A$7Lj6ƎLj5֟$4Ǝ8㌟|1Sb(l)A1bAz1bqş1Sa(l)A˔"Az˔"}T`2Sb(l)(,֬b(b`䢲2Sa(lr)[r΄ (fe׏,`3Sb(r)͏֬"͏,"ǎ쟎䢲3Sa(lr)[Ÿ΄ ,fe\84Sb(r)e"e"\24Sa(r)PbPb׏,L5Sb(r)͏Lfb͏,LfbǎfP5Sa(r)[ŸL ,feYʟL6Sb(r)(,Lf"(Lf"`fP6Sa(lr)[rL (fe㌟87Sb(l)AebAzebqş27Sa(l)AP"AzP"Bf2D8̏KЄfd ,12D9lKЄfd ,ʟ2\hA2(iBF2\dBF2eA2f2glaA8bOlc>˼iff?ff:q(400,800) :q(0,0)>τffffff?-'TheoKhandednessforeachorientedordouble-sidedpGositionisshownwithacharactersetinparentheses. 'TheUUoptionalargumentBONDLISTusescharacterslistedinT*able10.1soastospGecifydoublebonds.'Example:g\nonaheterohi[bjg]{1==N;3==N;5==N;7==N}{1==H;5==H;4D==O}g\nonaheterohi[bjge]{1==N;5==N;7==N}%{1==H;3==C$_{6}$H$_{5}$;4==NHCH$_{3}$}g\nonaheterohi[bjge]{1==S;2==N}{3==Cl}'proGduceUUthefollowingstructures:󧍍SպU@ջ[@fd@[@KЄfdPSպTU@'To^xfeSպ2lU@ wt 2|To TSպ2TU@[Tt 2|r#[q[@fd@^U䟢dfd f^UĘfdW"$TWU TN]hNlNN]$NlLjN:;ןfHCo1fd (ufPHsLnTsTL"Oz Әfd8z 2vfd8,uջufdPuKЄfdP,Tu'T"3fe,2lu w`2|Tş T,2Tu[T`2|z5[qufd@٭dfd٭Ęfdyɟ$Tҭ T-w+ FhNF$NLjN fHG1fd (ݟC6|sH5şG-L"NHCH3`efd8J$Jp6Vjfd@RjKЄfdPJ$TLj'Tf7ȟ"3feH2|Lj j2|Tfj TH2|TLj[qTj2|fj[qRjfdPVjdfd fUNĘfdLPTNTfdGhSN韡NlkClfjgJTZ'ObM'84BFUJIT*AUUShinsaku:qXMTU>'ExX'fe>|2UoHObM2O-'UChapter 112E'TBuilding T{Blo c8ks:E'11.1*'Six-Membs3eredffBlocksg'Themacro\sixunitvprovidesasix-membGeredfragmentthatcanbGefusedtoanotherringstructure, 'proGducingUUanewringsystem.a \sixunitv[BONDLIST]{ATOMLIST}{SUBSLIST}{OMIT}H'ThemoGdesofnumberingforpositionsandforedgesarethesameasthoseof\sixheterov.Hence,/the'argumentsBONDLIST,A*TOMLIST,andSUBSLISTarewritteninthesameway*.OUTheargumentOMIT'indicates2bGondstobedeleted,9wherecharactersareselectedfromthetablepreparedfortheBONDLIST'of|\sixheterov.);ItshouldbGenotedthattheassignmentofanullargumenttoA*TOMLISTlproGducesa'carbGocyclicUUbuildingbloGck.H'Example: \sixunitv[b]{1==N}{1==H;2==Cl}{d}?\qquad \sixunitv[b]{}{1D==O;2==Cl}{d}H'proGduceUUthefollowingstructures:db5bɧb0ݲPfe"5b"tݲPfev"ɧ"VfeޟexNޟHReX ,fe5òBCl5bɲZ"5'"redbɧb%XǟݲPfer""% ݲPfe red"X=ɧ"" feXuO ed8fer!ed8fe2-òBCl%ɲZ"')'" 'The[macro\sixunithisthehorizontalcounterpartof\sixunitv. iItproGducesasix-membGered 'fragmentUUofhorizontaltypGe, \sixunith[BONDLIST]{ATOMLIST}{SUBSLIST}{OMIT}Yx'Example: \sixunith[b]{1==N}{1==H;2==Cl}{d}?\qquad \sixunith[b]{}{1D==O;2==Cl}{d}H'proGduceUUthefollowingstructures:K85VoObM'86BFUJIT*AUUShinsaku:qXMTU>'ExX'fe>|2 uPh:[h:fdP`ThkTh:LpfdPpTh:(eTޟefd[ۙNџH 2fd (hBClh:催T4Tq۟`џkџfdP' `T"!kTџLpfdPq۟`Tџ(UTXuefdKOqeʄfd8qZfd8BClџ催TT"⍍'11.2*'Five-Membs3eredffBlocks;'Thefmacro\fiveunitvproGducesa ve-memberedffragmentthatcanbGefusedtoanotherringstructure 'toUUproGduceanewringsystem.ɍ \fiveunitv[BONDLIST]{ATOMLIST}{SUBSLIST}{OMIT}W'The YnumbGeringofpositionsandthedesignationofedgesarethesameasthoseof\fiveheterov.YHence,'thehargumentsBONDLIST,A*TOMLIST,andSUBSLISTAarewritteninthesameway*.:Theargument'OMIT?indicatesTbGondstobedeleted.UrItisalistofthesameformatastheBONDLIST?of\fiveheterov.W'Example: \fiveunitv[b]{1==N}{1==H;2==Cl}{d}?\qquad \fiveunitv[b]{}{1D==O;2==Cl}{d}W'proGduceUUthefollowingstructures:c"hP"0ݲPfe匄fd"3vbrPbVfeޟNޟHR؄ ,fe5Cl5b㲪b5br""%XǟݲPfeX=匄fd"3 rbX=b" feXuO ؄8fer!؄8fe2-Cl%㲪b')b 'TheRmacro\fiveunitviproGducesa ve-memberedRfragmentofinversetypGethatcanbefusedto 'anotherUUringstructuretoproGduceanewringsystem. \fiveunitvi[BONDLIST]{ATOMLIST}{SUBSLIST}{OMIT}<'Example: \fiveunitvi[b]{1==N}{1==H;2==Cl}{d}?\qquad \fiveunitvi[b]{}{1D==O;2==Cl}{d}W'proGduceUUthefollowingstructures:cb5bɧb0ݲPfe܄fd"3v"ɧ"VfeޟexNޟHReX ,fe5òBCl5bɲZ"5'"redbɧb%XǟݲPfeX=܄fd"3 red"X=ɧ"" feXuO ed8fer!ed8fe2-òBCl%ɲZ"')'"WwɠObM'CHAPTERUU11.BUILDINGBLOCKS傲87'fe>|2  'The^macro\fiveunithisa ve-membGered^fragmentofhorizontaltypGethatcanbefusedtoanother 'ringUUstructuretoproGduceanewringsystem.ʐ \fiveunith[BONDLIST]{ATOMLIST}{SUBSLIST}{OMIT}4'Example: \fiveunith[b]{1==N}{1==H;2==Cl}{d}?\qquad \fiveunith[b]{}{1D==O;2==Cl}{d}썑'proGduceUUthefollowingstructures:cOPTh[Th:fdP5>"3feOph(eޟefdhۙNhHȵ2fd ,hBClh催ڟ' `T"!kTџfdP>"3fe' `"!(UXuefd<O- eʄfd8- Zfd8(9BCl"!催#q 'Theumacro\fiveunithiistheinverseucounterpartof\fiveunith.\&ItproGducesa ve-membGered'fragmentFofanotherhorizontaltypGesothatitcanbefusedtoanotherringstructuretoproduceanew'ringUUsystem.ʐ \fiveunithi[BONDLIST]{ATOMLIST}{SUBSLIST}{OMIT}4'Example: \fiveunithi[b]{1==N}{1==H;2==Cl}{d}?\qquad \fiveunithi[b]{}{1D==O;2==Cl}{d}썑'proGduceUUthefollowingstructures:cPh:[h:fdP5X>"3fepTh:(eTޟefd[ۙNџH 2fd (hBClh:催T4Tq۟`џkџfdP">"3feq۟`Tџ(UTXuefdKOqeʄfd8qZfd8BClџ催TT"q'11.3*'SettingffLos3cantNumbs3ersEZ'TheUU\bdloocantprintssixcharactersontheedgesofasix-membGeredringofverticaltypGe(locant.sty).'\bdloocant{#1}{#2}{#3}{#4}{#5}{#6}'On~6theotherhand,=the\bdloocnthprintssixcharactersontheedgesofasix-membGeredringofhorizontal 'typGe.'\bdloocnth{#1}{#2}{#3}{#4}{#5}{#6}4'Example:XObM'88BFUJIT*AUUShinsaku:qXMTU>'ExX'fe>|2 '\bdloocant{a}{b}{c}{d}{e}{f}?\qquad '\bdloocnth{a}{b}{c}{d}{e}{f}qč'proGduceUUthefollowingstructures:`d덍ağXbc f]XedqΟ@ar b&rc@c&rcdrecf 'TheUU\sxloocantprintssixcharactersontheverticesofasix-membGeredringofverticaltypGe.'\sxloocant{#1}{#2}{#3}{#4}{#5}{#6}'OnŴtheotherhand,!the\sxloocnthprintssixcharactersontheverticesofasix-membGeredringof'horizontalUUtypGe.'\sxloocnth{#1}{#2}{#3}{#4}{#5}{#6}*'Example:'\sxloocant{1}{2}{3}{4}{5}{6}?\qquad'\sxloocnth{1}{2}{3}{4}{5}{6}'proGduceUUthefollowingstructures:`d덍p1=82=t3p48t5886q۟h1 q82u̟83"uh4 q6u̟5 'These>commandscanbGeusedbycombiningwithastructure-drawingmacroinapictureenvironment'toUUshowtheloGcantnumbGeringofthestructure.⍑'Example:'\begin{picture}(1000,1000)(0,0)'\put(0,0){\sxloocant{1}{2}{3}{4}{5}{6}}'\put(0,0){\bdloocant{a}{b}{c}{d}{e}{f}}'\put(0,0){\bzdrv[c]{1==OH;2==C(CH$_{3}$)$_{3}$;4==OH}}'\end{picture}'proGducesUUthefollowingstructure:leƣ1p82pt3ƣ4kt5k86˟aXb˟cʸIfTXe8IdƧed"Ŭɟɧ"ƧedbɧbƧbŬɟbƧ""SݲPfeyݲPfeʓu崮ӭOH֓ued8fe๟òBC(CH3|s)3ɲZ"ൟ'"ӭOH֓u؄8feYΠObM2 'UChapter 122'TFurther T{CyclicComp ounds:'12.1*'DrawingffChairFformofCylohexane'The-macro\chairisusedtodrawcyclohexanederivqativesofchair-form(ccycle.sty).dXTheformatofthis 'commandUUisasfollows:i \chair[BONDLIST]{SUBSLIST}'LoGcantUUnumbersUUfordesignatingsubstitutionpositionsarerepresentedbythefollowingdiagram:W\j@tAJPdAJPSJPSESADACAAEˎncPՎøP܏h Ph2S׏h2SՏ$p=Sˏ$Һ$N$e$ܺAԑAJTPAJکPAOPAJP"ڪܣ'"h͟1Se(l)Pfe1Sa(l)ADbmby42Se(l)\fTfeN2Sa(r)ˎbb3Se(l)[ʟfe3Sa(lr)h2"u["gN4Se(l)\6Bfe\$4Sa(l)Տ$ebğ {b`5Se(l)[efeя2$5Sa(l)Atb[bAr2|6Se(l)̄fev6Sa(r)Yff?ff:q(400,240):q(0,0)>τffffff?A܍'Each/charactersetinparenthesesrepresentsthehandednessofthecorrespGondingpostion,7$whichis xed'inUUthistypGeofmacros. 'The=optionargumentBONDLIST=yisancharacterstringinapairofbrackets,uwhereeachcharacterindi-'catesthepresenceofadoublebGondattheedgecorrespondingtothecharacter.56Thebond-correspondence'isVratherarbitraryinsomecasesbutconformstochemicalconventionsasfaithfullyaspGossibleifsuch'conventionsUUarepresence(T*able12.1). L΍b:T*ableUU12.1:qArgumentBONDLISTforcommandsnchair@ML͉ffԤfdCharacter=cPrintedUUstructureffԡnone=ccyclohexanea=c1,2-doubleUUbGondb=c2,3-doubleUUbGondc=c4,3-doubleUUbGondd=c4,5-doubleUUbGonde=c5,6-doubleUUbGondf=c6,1-doubleUUbGondffԎ׍ 'TheargumentSUBSLISTforthismacrotakesageneralformat,YexceptthatmoGdi ersareselected'from$`Sa'foranaxialsubstitutent,$a`Se'foranequatorialsubstitutent,$aand`D'forasubstitutentthrough'anUUdoublebGond.K89ZaObM'90BFUJIT*AUUShinsaku:qXMTU>'ExX'fe>|2 'Example:Zu'\chair{1D==O;2Se==H$_{3}$C;2Sa==CH$_{3}$;% '6Se==CH$_{3}$;6Sa==CH$_{3}$}?\qquad\qquad'\chair[b]{1D==O;4Se==CH$_{3}$;4Sa==CH$_{3}$}؍'proGduceUUthefollowingdiagrams:R%(1PS,1PS.uES6(uD@(uCJ(uT(uETu^uncPhuøPovO PqO2SjvO2Shv p=S^v ҺTv NJv e@v ܺ@(ԑ%(1TP/(1کP6(OP`ߟ$O(-T@'T@(5L@(L@,(uDb'՟mbݟeH3|sC5CfTfe25CH36(tb1[b/(Y2|CH3?k̄fe<]ܲCH3jPSjPSESDCEncP øP͈ PM2S ͈2S Dp=SDҺDNDeDܺ֟ԑjTPjکP֟OP4C$OfT@6T@nL@>L@͈2"!4(u[",ȟCH3VBfeDCH3"N'12.2*'DrawingffBicyclo[2.2.1]heptaneM'The@macro\bicychepvisusedtodrawbicyclo[2.2.1]heptanederivqativesofverticaltypGeina atfashion.'TheUUformatofthiscommandisasfollows: \bicychepv[BONDLIST]{SUBSLIST}؍'LoGcant_numbers_fordesignatingsubstitutionpositionsandbonddescriptorsforassigningdoublebonds'areUUshowninthefollowingdiagram:dMA6tA֟dA֟ed"'ɧ"A֟edb[ɧbA֟b'bA֟"["(ݲPfeƟݲPfeA֟֟ۄݙ:A֟edC֟edCۄCc⟯1Sb(l)A֟edTedT[1Sb(r)A֟edu&ed 2Sb(r)[ɲZǏDzZ"02Sa(r)[匄fd8 3Sb(r)[粪TǏ鲪T"3Sa(r)[܄fd8c4Sb(l)A֟[4Sa(r)A֟Tu&T5Sb(l)'粪鲪zC5Sa(l)'܄fd86Sb(l)'ɲZTDzZTzC06Sa(l)'匄fd8Aҟ1E82Et3Aҟ4At5A86AaB&XbAc3xfϿXexd͟ff?ff:q(400,240):q(0,0)>τffffff?'Each/charactersetinparenthesesrepresentsthehandednessofthecorrespGondingpostion,7$whichis xed'inUUthistypGeofmacros. V 'TheYoptionargumentBONDLIST?isancharacterstringinapairofbrackets,whereeachcharacter'indicatesUUthepresenceofadoublebGondattheedgecorrespondingtothecharacter(T*able12.2).`moL΍2߽T*ableUU12.2:qArgumentBONDLISTforcommandsnbicychepvandnbicychephLML͉ffԤfdCharacter=cPrintedUUstructureffԡnone=ccyclohexane a=c1,2-doubleUUbGondb=c2,3-doubleUUbGondc=c4,3-doubleUUbGondd=c4,5-doubleUUbGonde=c5,6-doubleUUbGondf=c6,1-doubleUUbGondA=caromaticUUcircle7=c7,7-dimethylffԎ[wObM'CHAPTERUU12.FUR*THERCYCLICCOMPOUNDSE91'fe>|2  'TheargumentSUBSLISTforthismacrotakesageneralformat,pinwhichthemoGdi erslistedinT*able '2.2UUareused.7'Example:JY'\bicychepv{2D==O}'\bicychepv[b]{2==OMe;3==OMe}'\bicychepv{3B==OH;2A==OH}'\bicychepv[7]{1==CH$_{3}$;2==OH}7'proGduceUUthefollowingdiagrams:c=Yed"Rɧ"cedbjΟɧbYbRbc"jΟ"tݲPfeRwݲPfecfDf^ݙ:cedCfDedCf^CòBOt$"v0"u+˘"w+̟e"ed"ɧ"edb5cɧbbb"5c"1ݲPfeuݲPfe3ݙ:edCedC3CĵWfe5òBOMe5cɲZ"5'"5޲OMe5c㲪b5bred"X<ɧ" redbɧbrbX<b r""XƟݲPfe% ݲPfe r  ȟݙ: redC edC ȟC(,޲OH㲪b(b(,òBOH%̎tl̎V ̎ J8Ą̎"p̎#̎%nޟȄ̎'%t̎Sȯed"Lџɧ"]ȯedbd⍟ɧbSȯbLџb]ȯ"d⍟"n[ݲPfeL{ݲPfe]ȯ`H`b]ݙ:]ȯedC`HedC`b]C[ANb]NZ CH3]}ed8fe{òBOHn⍟ɲZ"p⽟'" 'The{Qmacro\bicychephisusedtodrawbicyclo[2.2.1]heptanederivqativesofverticaltypGeina at 'fashion.qTheUUformatofthiscommandisasfollows: \bicycheph[BONDLIST]{SUBSLIST}'LoGcantnumbersfordesignatingsubstitutionpositionsalongwithbonddesciptorsarefoundinthefol- 'lowingUUdiagram:c=A6tA`dA`kA`T(UTҟ`TÎܟkTҟ`Îܟ(UfdPLpfdPA`A`l-ҟ`Xҟ`Xl-Xzt1Sb(l)A`bAf-bzt1Sb(l)A`"Af2"}@2Sb(l)催b\ŲObHB2Sa(lr)[Z傄8feя3Sb(r)Îܟ催"ŏ ŲO"ԟB3Sa(lr)[傄8feݏD4Sb(r)ҟ`"-"ݏD4Sa(r)ҟ`b2bяr5Sb(r)Îܟ>bŏ LqbԞ345Sa(lr)[v8fe}@r6Sb(l)>"\Lq"H346Sa(lr)[Zv8feAh1AŸ82E83Eh4AŸ6E5A@aAޟ bB.@cB.dAޟe3`f͟ff?ff:q(240,400):q(0,0)>τffffff?'Each/charactersetinparenthesesrepresentsthehandednessofthecorrespGondingpostion,7$whichis xed'inUUthistypGeofmacros.qF*ortheSUBSLISTandtheBONDLIST,seeTable2.2and12.2.q.7'Example:'\bicycheph{2D==O}'\bicycheph[b]{2==OMe;3==OMe}'\bicycheph{3B==OH;2A==OH}'\bicycheph[7]{1==CH$_{3}$;2==OH}7'proGduceUUthefollowingdiagrams:[=`Cp`HfkCp`THf(UTf^`TbkTf^`b(UNffdPNfLpfdPCp`Mp`Nl-b^`XX^`XXl-XA2BOG^02PTF*2PTI:ƘTHĘT%`hk%`Th(UTa`ThkkTa`hk(UhfdPhLpfdP%`%`hCl-a`Xa`XhCl-Xefdg矶BOMeh催T4˟ThBOMehk催qڟ`Пkqڟ`TП(UT `T kT ` (UПfdPПLpfdPqڟ`qڟ`l- `X `Xl-X8BOH 傭pBOHXjK̎Qŕ̎IŸ$̎Bn'B̎;p`̎3Ɵ~̎,r̎%K̎Uȏ`ZkUȏ`TZ(UTxb˟`Tt՟kTxb˟`t՟(U`fdP`LpfdPUȏ`_ȏ``l-tb˟`Xjb˟`Xjl-Xi΄̎i岄̎2şCH3GW2fd8SQBOHZ催TX5T\ʠObM'92BFUJIT*AUUShinsaku:qXMTU>'ExX'fe>|2  'F*orugthepurpGoseofdepictingthestereochemistyugofbicyclo[2.2.1]heptanederivqatives,}lyouugcanusethe 'command0\bornaneinsteadofthecommands\bicychepvand\bicycheph.0fTheformatofthiscommand'isUUasfollows:덑 \bornane[BONDLIST]{SUBSLIST}p'LoGcantUUnumbersUUfordesignatingsubstitutionpositionsarerepresentedbythefollowingdiagram:钍j@t~@Pd~@P @Q A L aLatLa&L (̎tL. tL. uL. KaKaFKaFK FK Z ( A ~A ~@ GKLHKL&KLFK WK AIJ1􌟧ğğ~r7Sb(r)􌟧ZTZmݟ~r7Sa(l)Kެ؟KŽ؟˰2Sb(r)Kݬa؟vaÎܟ嚲2Sa(r)tL.!uֲ!u"ղ3Sb(r)t.Zu.Zuh3Sa(r)L |L p4t@Pap@ŸeaTe5Sb(l)t@Pp@ŸPV$K5Sa(l)|AZx@⟼Z]2~Ҳ6Sb(l)|A!x@Ř!]$gȘ6Sa(l)Yff?ff:q(200,240):q(0,0)>τffffff?"'Each/charactersetinparenthesesrepresentsthehandednessofthecorrespGondingpostion,7$whichis xed'inUUthistypGeofmacros.={ 'TheYoptionargumentBONDLIST?isancharacterstringinapairofbrackets,whereeachcharacter'indicatesSthepresenceofadoublebGondattheedgecorrespondingtothecharacter(T*able12.3).lThe'SUBSLISTUUformatisshowninT*able2.2.'oL΍]=T*ableUU12.3:qArgumentBONDLISTforcommandsnbornaneLML͉ffԤfdCharacter=cPrintedUUstructureffԡnone=ccyclohexane a=c1,2-doubleUUbGondb=c2,3-doubleUUbGondc=c4,3-doubleUUbGondd=c4,5-doubleUUbGonde=c5,6-doubleUUbGondf=c6,1-doubleUUbGondg=c1,7-doubleUUbGondh=c4,7-doubleUUbGondffԎ)3e'Example:'\bornane{2D==O}'\bornane[b]{2==OMe;3==OMe}\par'\bornane{3B==OH;2A==OH}'\bornane{7Sa==CH$_{3}$;7Sb==CH$_{3}$;1==CH$_{3}$;2==OH}p'proGduceUUthefollowingdiagrams:]ÈObM'CHAPTERUU12.FUR*THERCYCLICCOMPOUNDSӲ93'fe>|2 gE qE tןB1 ~ןLYaןLXaN1LWa~gqLZ(̎N1L~ N0L~ NRL~ gL.agL/a瑟L0a|瑟L r瑟L o3 x kfP ggP gEP 璟L L~瓟L L~qL Lg4!h'e!(!)e!h/嶲Oqʟ qʟ %\B1 %\LYa%\LXaLWa LZ(̎$L~ (L~ (ןL~ "pL.apL/a?L0a ?L ?L x qP qP qʟP ?L L?L L>L L# Ln % /Ln ,pL.!2!=嶲OMe$L~!*!5OMeeGgE qE tןB1 ~ןLYaןLXaN1LWa~gqLZ(̎N1L~ N0L~ NRL~ gL.agL/a瑟L0a|瑟L r瑟L o3 x kfP ggP gEP 璟L L~瓟L L~qL LNm:OH˟̎ҟf̎gٟP̎'̆̎̎2̎g(̎'^̎L̎h/OHgL.!h+!qʟ qʟ %\B1 %\LYa%\LXaLWa LZ(̎$L~ (L~ (ןL~ "pL.apL/a?L0a ?L ?L x qP qP qʟP ?L L?L L>L L%\Z%$Z̟~²CH3%\%%~²CH3?L ?'L rVCH3,pL.!2!=嶲OH!5c'12.3*'DrawingffAdamantaneDerivatives󚍑'TheUUmacro\adamantaneprintsadamantanederivqativesbymeansofthefollowingformat:ۍ \adamantane[BONDLIST]{SUBSLIST}%'whereUUBONDLISTisnote ectiveinthepresentspGeci cation.AtAdCACAҟCAꟘPHA꟝PHBJPHAꟘPA꟝PAPAҟ(ZAҟ(ZAr(ZArrJBJB2Aҟ(Aҟ(B2(bCBbCBJCACCCAB(B(Bb(B(ZB(ZA(ZAYh1AZtdZBzh3BJBdB(DB(DB5Aӟ(AƟ(A͟7ꟓPCFC 2bAꟓP[A 2aBb\zBb4bBb~Z؏XyZB 4aA!в6bAZ!ZBв6arCΟzC78bAr~|yA@ 8aA[FzA9bA~yA$9a2CɨzC10bB2~Z̏(yZBJ$10aff?ff:q(550,300) :q(0,0)>τffffff?R'TheUUargumentSUBSLISTisslightlydi erentfromgeneralconventions,asshowninT*able12.4.͍hYAT*ableUU12.4:qArgumentSUBSLISTforcommandnadamantane:̍^<ffufdCharacterxudPrintedUUstructureffuforUUn=1;3;5;and7(bridgeheads) nUUorna=cexoGcyclicUUsinglebondatn-atomffuforUUn=2;4;6;8;9;and10(bridges) na=cexoGcyclicUUsinglebondatn-atom(axial)nb=cexoGcyclicUUsinglebondatn-atom(equatorial)nD=cexoGcyclicUUdoublebondatn-atom(2and6)ffu^ObM'94BFUJIT*AUUShinsaku:qXMTU>'ExX'fe>|2 'Example:m3'\adamantane{2D==O;6D==O} '\adamantane{2D==O;6D==O;1==F;3==Cl}獑'proGduceUUthefollowingdiagrams:aICIC1CIPHIPHPHIPIP韟P1(Z1(Zџ(Zџџ韩1(1((ÛCCC韩C音CCIIaa(a((a(Za(Z(ZOߟP feOP feߟ̀ feÒ fe3 OVCrVCr>CrVPH#rVPH'rPHrVPrVPqP r>(Zr>(Zqޟ(Zqޟޟ.򶟩,r+rr>(r>(!r(4ΟC2rΟC1rCqCCCrVVnrn()rn(-rΟ(rn(Z rn(Zr(Z?O 쟓P fer\P fe ̀ fer\̀ fe?3 OꨟhFqZdZ=r柙hCl1r2?d"*'12.4*'DrawingffFfuranosesandPyranoses'F*orUUdrawingfuranoses,thecommandfuranoseisused.qTheformatofthiscommandisasfollows: \furanose[BONDLIST]{SUBSLIST}'LoGcantnumbersfordesignatingsubstitutionpositionsandbonddescriptorsarerepresentedbythefol- 'lowingUUdiagram:d`ZA6tA`dA`"A`"ێk"u`bu`bۦkbA`TA`TAƟ`TununuAƟf3ێ,OBl` feB^,1Sb(r)Bl\ feB^1Sb(r)B< feX|2SbB<̬ feB.2Sa(r) fe|3Sb̬ fe:3Sa(lr)d` fe&,4Sb(l)d\ feX_4Sa(l)͟ff?ff:q(240,400):q(0,0)>τffffff?'Each/charactersetinparenthesesrepresentsthehandednessofthecorrespGondingpostion,7$whichis xed'inUUthistypGeofmacros. [M 'TheYoptionargumentBONDLIST?isancharacterstringinapairofbrackets,whereeachcharacter'indicatesUUthepresenceofadoublebGondattheedgecorrespondingtothecharacter(T*able12.5).i̍L΍2߽T*ableUU12.5:qArgumentBONDLISTforcommandsnbicychepvandnbicycheph:ML͉ffԤfdCharacter=cPrintedUUstructureffԡnone=cmotherUUskeleton a=c1,2-doubleUUbGondb=c2,3-doubleUUbGondc=c4,3-doubleUUbGondd=c4,5-doubleUUbGonde=c5,1-doubleUUbGondffԎ_̠ObM'CHAPTERUU12.FUR*THERCYCLICCOMPOUNDSӲ95'fe>|2  'TheargumentSUBSLISTforthismacrotakesageneralformat,pinwhichthemoGdi erslistedinT*able '2.2UUareused.M!'Example:f׍'\furanose{1Sa==H;1Sb==CH$_{2}$OPO(OH)$_{2}$;2Sb==\lmoiety{HO};3Sa==OH;%'4Sb==(HO)$_{2}$OPOH$_{2}$C;4Sa==HO}\hskip5cm'\furanose[b]{1D==O;2Sa==OH;3Sa==\lmoiety{HO};4Sb==HOH$_{2}$C(HO)HC}M!'proGduceUUthefollowingdiagrams:[YލY `"c `"g>k"`bz`bw>kbY `T_ `T_<`Te,O\ feԟH` feԟ,CH2|sOPO(OH)2 few|HOeq ̬ febpOHYpڟ` feΟ,(HO)2|sOPOH2CYpڟ\ feM-HO?`"I`"Mk"k`ba`b]kb?`TE`TE#`Ti˟o˟oK#f3W,ON/2҄fd3uٲfd 0uֲfd 0/lOh陟̬ fee鋟OHK̬ fe@HO?` feؚ,HOH2|sC(HO)HC 'F*orUUdrawingfuranoses,thecommandpyranoseisused.qTheformatofthiscommandisasfollows: \pyranose[BONDLIST]{SUBSLIST}'LoGcantUUnumbersUUfordesignatingsubstitutionpositionsarerepresentedbythefollowingdiagram:cYA6tA`dA`A`AƟ`AƟ2Bfd3u`Tޟ`TA`TA`TAƟ`TununuAƟf3ub OBl` feB^,1Sb(r)Bl\ feB^1Sb(r)B< feX|2SbB<̬ feB.2Sa(r) fe|3Sb̬ fe:3Sa(lr)d` fe&,4Sb(l)d\ feX_4Sa(l) fe5Sb(l) fe\5Sa(l)͟ff?ff:q(240,400) :q(0,0)>τffffff?%N'Each/charactersetinparenthesesrepresentsthehandednessofthecorrespGondingpostion,7$whichis xed 'inUUthistypGeofmacros.  'TheYoptionargumentBONDLIST?isancharacterstringinapairofbrackets,whereeachcharacter'indicatesUUthepresenceofadoublebGondatthecorrespondingedge(T*able12.6).杍L΍2߽T*ableUU12.6:qArgumentBONDLISTforcommandsnbicychepvandnbicycheph@ML͉ffԤfdCharacter=cPrintedUUstructureffԡnone=cmotherUUskeleton a=c1,2-doubleUUbGondb=c2,3-doubleUUbGondc=c4,3-doubleUUbGondd=c4,5-doubleUUbGonde=c5,6-doubleUUbGondf=c6,1-doubleUUbGondffԎ! 'TheargumentSUBSLISTforthismacrotakesageneralformat,pinwhichthemoGdi erslistedinT*able'2.2UUareused.M!'Example:`qObM'96BFUJIT*AUUShinsaku:qXMTU>'ExX'fe>|2 '\pyranose[a]{3Sb==OAc;4Sa==AcO;5Sb==CH$_{2}$OTs} '\pyranose[b]{2D==O;5Sb==CH$_{2}$OTs}'proGduceUUthefollowingdiagrams:Z%`%`U`U2Bfd3O-`Tʵm`T%`T%`TU`TNNO-Uf3N Oş# fe|OAc\ feAcO# feCH2|sOTsqڟ`qڟ`r `r 2Bfd3)`T& "`Tqڟ`Tqڟ`Tr `T#))r f3 O r2҄fd3/ٲfd 0/ֲfd 0<lO>\ fe4AcO>؟ fe>ʟCH2|sOTsaaObM2. 'UChapter 132$ 'TAliphatic T{Comp ounds:$ '13.1*'DrawingffTfetrahedralUnits*0'TheT;macro\tetrahedralisusedtodrawatetrahedralunit(aliphat.sty).qiTheformatofthiscommand 'isUUasfollows:- \tetrahedral[AUXLIST]{SUBSLIST}l"'TheUUfollowingdiagramshowsthenumbGeringfordesignatingsubstitutionpositions:cTA6tAdAL1|@ (feA]Lb2Ab2fd8AL3|̐ (feALb4AŸ2fd8ALb0͟ff?ff:q(300,300):q(0,0)>τffffff?DO'inUUwhichthesamemacroisusedtotypGesetbothsaturatedandunsaturatedderivqatives. $ 'TheroptionalargumentAUXLISTrKisusedtospGecifyachargeonthecentralatom:_i.e.,f0+grepresents'aUU+charge(oranotheronechararacter)onthecenter. 'TheV!argumentSUBSLISTUisusedtospGecifyeachsubstituentwithaloGcantnumbGerandabondmodi er'shownUUinT*able13.1,inwhichnisanarabicnumeralbGetween1and4.mL΍fT*ableUU13.1:qSUBSLISTforntetrahedral4wL͉fffdCharacterSStructuresUUprintedffnT=ctripleUUbGondatn-atom nD=cdoubleUUbGondatn-atomnUUornS=csingleUUbGondatn-atomnA=calphaUUsinglebGondatn-atomnB=cbGetaUUsinglebondatn-atomffz[ 'TheZcentralcarbGonatomisasignedbywriting0==C.Thestructuralformulaofanammoniumion'canUUalsobGeobtainedwiththiscommand.l"'Example:K97bObM'98BFUJIT*AUUShinsaku:qXMTU>'ExX'fe>|2 '\tetrahedral{0==C;1==H;2==Cl;3==F;4==Br}\qquad '\tetrahedral{0==C;1D==O;2==Cl;4==Cl}\qquad'\tetrahedral[{}{0+}]{0==N;1==H;2==CH$_{3}$;3==H;4==H}uL'proGduceUUthefollowingstructures:Fh͟LbC͟LH@ (ferŌLbCl}ő2fd8͟LF̐ (fe-LbBr2fd8ƿLbCƿLOF˟@ (feo@ (fe~LbClƃ2fd8LbCl2fd85{t+,DZLbN,DZLH0@ (fe LbCH3u2fd8,DZLH0̐ (feDLbH5՟2fd8 'Themacro\squareisusedtodrawatetrahedralunitofanothertypGe(aliphat.sty).cITheformatof 'thisUUcommandisasfollows: \square[AUXLIST]{SUBSLIST}'TheUUfollowingdiagramshowsthenumbGeringfordesignatingsubstitutionpositions:bhsA6tAdL1ALBALBL2Aά@A@L3AάArL4ALB@ArLB@ALb0͟ff?ff:q(300,300):q(0,0)>τffffff?!'Example:'\square{0==C;1==H;2==Cl;3==F;4==Br}\qquad'\square{0==C;1D==O;2==Cl;4==Cl}'proGduceUUthefollowingstructures:FhFLbCFLHfLBƎLBFLClfά@Ǝ@*LFBάyFLBrBLB@LB@8LbCGLO eܬ e Ÿ2 2GLCl Xά@ ǀ@z9LCl4LB@ LB@ 荍'13.2*'DrawingffTfrigonalUnits'Themacro\rtrigonaland\ltrigonalareusedtodrawright-handedandleft-handedtrigonalunits'(aliphat.sty).qTheUUformatsofthesecommandsareasfollows: \rtrigonal[AUXLIST]{SUBSLIST} \ltrigonal[AUXLIST]{SUBSLIST}'ThebGondanglesof2{0{3are90^ O!cmsy7inthetrigonalunitsprintedwiththesecommands.VThearguments'AUXLISTUUandSUBSLISTarethesameasthoseof\tetrahedral.'Example:'\rtrigonal{0==C;1D==O;2==Cl;3==F}\qquad'\ltrigonal{0==C;1D==O;2==Cl;3==F}csObM'CHAPTERUU13.ALIPHA*TICCOMPOUNDSE99'fe>|2 'proGduceUUthefollowingstructures:GvFLbCLbO fd8 fd8FLClfά@Ǝ@FLFfLBƎLB8LbCǘLbO \fd8 \fd8z9LCl4LB@ LB@LF4ά c 'Themacros\utrigonaland\Utrigonalareusedtodrawupwardtrigonalunitswithangles90^|and '120^9(aliphat.sty).qTheUUformatsofthesecommandsareasfollows: \utrigonal[AUXLIST]{SUBSLIST} \Utrigonal[AUXLIST]{SUBSLIST}'TheUUargumentsAUXLISTandSUBSLISTarethesameasthoseof\tetrahedral.c'Example:'\utrigonal{0==C;1D==O;2==Cl;3==F}\qquad'\Utrigonal{0==C;1D==O;2==Cl;3==F}'proGduceUUthefollowingstructures:GvFLbCFLOFR̐ (fe̐ (feFLClfLBƎLB*LFBLB@LB@8LbC8LOGD̐ (fe ̐ (fenjL*Cl XLB"" "BL*F-LBbʟ b 'On0Ntheotherhand,g themacros\dtrigonaland\Dtrigonalareusedtodrawdownwardtrigonal'unitsUUwithangles90^9and120^(aliphat.sty).qTheformatsofthesecommandsareasfollows: \dtrigonal[AUXLIST]{SUBSLIST} \Dtrigonal[AUXLIST]{SUBSLIST}'TheUUargumentsAUXLISTandSUBSLISTarethesameasthoseof\tetrahedral.c'Example:'\dtrigonal{0==C;1D==O;2==Cl;3==F}\qquad'\Dtrigonal{0==C;1D==O;2==Cl;3==F}'proGduceUUthefollowingstructures:GvFLbCFLOFR@ (fe@ (feFLClfά@Ǝ@*LFBά8LbC8LOGD@ (fe @ (fenjCl Xάb"]bBF-ά"ʟ]"!⍍'13.3*'DrawingffEthyleneDerivatives$'Theqmacro\ethyleneisusedtodrawethylenederivqativeswithangles90^ Ȳ(aliphat.sty).uTheformatof'thisUUcommandisasfollows: \ethylene[BONDLIST]{ATOMLIST}{SUBSLIST}dObM'100=FUJIT*AUUShinsaku:qXMTU>'ExX'fe>|2 'TheUUfollowingdiagramshowsthenumbGeringfordesignatingsubstitutionpositions:^,A6tAdtfd8tfd8ALb1ALb2L1ALB@ArLB@L2AάArDL3Bά@BB@DL4BLBBBLB͟ff?ff:q(300,300) :q(0,0)>τffffff?tL΍cET*ableUU13.2:qBONDLISTfornethylene(SFtL͉fffdCharacterCStructuresUUprintedfffn+g=c+UUcharge(oranotheronechararacter)onn-atom d=cinnerUUdoublebGond(betweenUUcenters1and2)t=cinnerUUtriplebGond(betweenUUcenters1and2)ffɍ'The^argumentA*TOMLIST5isusedforgivingcentralatoms.KTheargumentSUBSLIST5isthesameas 'thatUUof\tetrahedral.'Example:'\ethylene{1==C;2==C}{1==F;2==Cl;3==H;4==Br}\qquad'\ethylene{1==C;2==C}{1==CH$_{3}$;2==H;3==CH$_{2}$OH;4==H}\par'\ethylene{1==C;2==N}{1==Ph;2==Ph;3==OH}\qquad'\ethylene[t{2+}]{1==C;2==N}{1==CH$_{3}$;2==CH$_{3}$;3==H}'proGduceUUthefollowingstructures:BJfd8Jfd8LbCRLbCڟLFLB@ʟLB@xLClάʟFLHrά@ƚ@FLBrrLBƚLB fd8 fd88LbCǔLbCDLCH34LB@ LB@9LH4ά .GޟLCH2|sOH#Ǵά@#ܟ@.GޟLH#ǴLB#ܟLB=Jfd8Jfd8LbCRLbNLPhLB@ʟLB@LPhάʟFLOHrά@ƚ@ 2„fd8 2fd8 2fd8fp+8LbCǔLbNDLCH34LB@ LB@DLCH34ά .GޟLH#Ǵά@#ܟ@ 'TheWmacro\ethylenev,Fwhichistheverticalcounterpartof\ethylene,Fisusedtodrawethylene'derivqativesUUwithangles90^9(aliphat.sty).qTheformatofthiscommandisasfollows: \ethylenev[BONDLIST]{ATOMLIST}{SUBSLIST}'TheUUfollowingdiagramshowsthenumbGeringfordesignatingsubstitutionpositions:^,A6tAdtLB8feLB8feALb1AL2L1AάArL2Aά@A@蟽K²3AKAKK²4AK@ArK@͟ff?ff:q(300,300):q(0,0)>τffffff?ejObM'CHAPTERUU13.ALIPHA*TICCOMPOUNDSE101'fe>|2 'Example:-'\ethylenev{1==C;2==C}{1==F;2==Cl;3==H;4==Br}\qquad '\ethylenev{1==C;2==N}{1==Ph;2==Ph;3==OH}\qquad'\ethylenev[t{2+}]{1==C;2==N}{1==H$_{3}$C;2==CH$_{3}$;3==H}!̍'proGduceUUthefollowingstructures:[ LB8fe,GLB8fe͟LbC͟LCyLFɟάšFLClά@@FK²HKKux͟K²BrɟK@šK@ޓLB8fe-9LB8feƿLbCƿLNMLPhƻάƓG LPhߟά@@G K²OHߟKK.LB8fe0LB8fe2LB8fe4{e+,DZLbC,DZLN E[LH3|sC!ǭά!Dž?GLCH34џά@4@?GK²H4џK4K 'Themacro\Ethylenevisusedtodrawethylenederivqativeswithangles120^(aliphat.sty).Itisthe 'verticalUUcounterpartof\ethylene.qTheformatofthecommandisasfollows: \Ethylenev[BONDLIST]{ATOMLIST}{SUBSLIST}'TheUUfollowingdiagramshowsthenumbGeringfordesignatingsubstitutionpositions:c 7A6tAdtLB8feLB8feALb1AL2ş1ά"0]"A2Aάb[]bAKβ3AK"[ W"şKβ4Kb0 Wb͟ff?ff:q(300,300) :q(0,0)>τffffff?"'Example:'\Ethylenev{1==C;2==C}{1==F;2==Cl;3==H;4==Br}\qquad '\Ethylenev{1==C;2==N}{1==Ph;2==Ph;3==OH}\qquad'\Ethylenev[t{2+}]{1==C;2==N}{1==H$_{3}$C;2==CH$_{3}$;3==H}!̍'proGduceUUthefollowingstructures:[ LB8fe,GLB8fe͟LbC͟LCvןF,)ά"~_]"!Clάb߷]b!KβHK"߷ W"r+KβBr,)Kb~_ WbޓLB8fe-9LB8feƿLbCƿLNsPh-ά"Q]"Phߟάb੟]bKβOHߟK"੟ W".LB8fe0LB8fe2LB8fe4{e+,DZLbC,DZLN H3|sC . ά"C]"ACH34џάb6ᛟ]bAKβH4џK"6ᛟ W"!M'13.4*'DrawingffCon gurations'Theqmacrostetrastereoanddtetrastereotypsetfragmentswhichshowacturalcon gurationofa'tetrahedralUUcarbGonindi erentmodesofpro8jections.qTheformatsofthesecommandsareasfollows: \tetrastereo[AUXLIST]{SUBSLIST} \dtetrastereo[AUXLIST]{SUBSLIST}f+ObM'102=FUJIT*AUUShinsaku:qXMTU>'ExX'fe>|2 'TheUUargumentsAUXLISTandSUBSLISTarethesameasthoseof\tetrahedral. 'TheUUfollowingdiagramshowsthenumbGeringfordesignatingsubstitutionpositions:a`ŏtd՟2՟`fe@1aŷeaE|2՟Ԅ $fe3!We![|4ϮtGd2`fe;@1`!ßQv!F2`؄<̎;3-ӟa˟QvaǛ4ǿff?ff:q(300,300):q(0,0)>τffffff?Ս'Example: 9'\tetrastereo{1==F;2==Cl;3==H;4==Br}\qquad'\dtetrastereo{1==F;2==Cl;3==H;4==Br}'proGduceUUthefollowingstructures:D$2$`feJ@F>aeaF|Cl$Ԅ $feJHn!Ʀe!ƪ|Br2`fe<@F`!ğQv!FCl`؄<̎τffffff?Ս'Example:'\ethanestereo{1==C;2==C}{1==F;2==Cl;3==H;4==Br;6==H;5==Ph}\qquad'\ethanestereo{}{1==OH;2==H;3==Ph;4==H;5==COR;6==H}'proGduceUUthefollowingstructures:Y@$2$2N$`feFLbCFKC_ʟ!ҟQv!F_؄<̎JCl,aڟQvaƪHn!Ʀe!ƪBr>aeaH$feJPh22N`fe`!ğQv!ןOH`؄<̎'ExXUUcanbGenested,recognizingeachinnerpictureenvironmentasaL5ffA͉TU>'ExXpicturebGox. 'AUUpictureenvironmentUUofL5ffA͉TU>'ExXissetupwiththefollowingstatement:gKqȍRH\beginfpictureg(L 0ercmmi7x;Ly·)(Sx;Sy·),pRH.RH.RH.RH\endfpictureg/'ThiscommandproGducesanLx|s7Ly{`areafordrawingastructuralformula,¹wheretheorigin(0,0)can'bGeUUshiftedbygivingdi erences(Sx;Sy·). 'TheoA\put(Px;Py·)commandplacesaninnerpicturebGox(e.g.,uafragmentcreatedbyamacroofthe'presentpapGer)sothatthereferencepointoftheinnerpictureislocatedonthe(Px;Py·)pointoftheouter'pictureUUenvironment.,'14.1.2-'ReferencePointsandInnerOrigins'AmacroofXMTU>'ExXisbasedonaninnerpictureenvironment,@whichhasanoriginalpGointfordrawing'a_structureandasetofsiftedvqalues.SuppGosethede nitionofthemacrocontainsaninnerpicture'environmentUUrepresentedby1c \beginfpictureg(`x;`y·)(sx;sy·).'ThepGoint(sx;sy·)oftheinnerenvironmentbGecomesthe(0,0)pointofthestructuregeneratedbythe 'macro.ϛThistpGointiscalledthereferencepointofthemacrointhepresentmanual.ϛOntheotherhand,'the-originoftheinnerenvironment-bGecamesthe(sx;sy·)pointofthegeneratedstructure.dItiscalled'theUUinneroriginofthemacro. 'F*orUUexample,thecommand\cyclohexanevgeneratesaskeleton,_l;/tϟdϟed"Ϭɧ"ϟedbୟɧbϟbϬbϟ"ୟ"{ݲPfeyݲPfeKFβ103hF`ObM'104>FUJIT*AUUShinsaku:XMTU>'ExX'fe>|2 'inwhichthesymbGolrepresentstheinneroriginandthesymbGolrepresentsareferencepGoint.The 'macroUU\cyclohexanevisde nedonthebasisofaninnerpictureenvironment:qq}G\beginfpictureg(800,?800)(-400,-240).U'Asaresult,theinneroriginisreferredtoasthe(400,200)pGointoftheresultingmacro;andtheinner'(400;240)UUpGointisregardedastheneworigin(0,0),whichisthereferencepGointofthemacro. \ 'EachjBmacroischaracterizedbythereferecepGointandtheinnerorigin,o}whichareshowninaframed'bGoxbesidethespeci cationofthemacro.hThereferencepointandtheinneroriginofeachmacroare'revealedbystating\origpttrueinthepreambleofamanuscript.HThen,5theyareprintedwiththe'symbGols#and;5andthevqaluesofthemappearonthedisplay*.݈For#example,Wtheabove#cyclohexane'structureUUistypGesetbythefollowingstatement:'{\origpttrue'\begin{center}'\cyclohexanev{}'\end{center}}U'orUUbyanequivqalentstatement:'\begin{xymspec}'\cyclohexanev{}'\end{xymspec}'14.1.3-'SettingCo`ordinates'The*command\puttypGesetsanob8ject, whichmaybGeacharacterstring, astructuregeneratedwitha'macro,orothers.5|Whenamacroiswrittenasanargumentofthecommand\putinanouterpicture'environment,aBstructureduetothemacroistypGesetsothatthereferencepointofthemacroisplaced'onUUthepGointdesignatedbythe\putcommand.qF*orexample,'{\origpttrue'\begin{picture}(1000,700)(0,0)'\put(0,0){\cyclohexanev{}}'\put(0,0){\circle{80}}'\put(400,240){\circle{80}}'\end{picture}'}U'proGducesQdPtƧdƧed"Ŭɟɧ"ƧedbɧbƧbŬɟbƧ""SݲPfeyݲPfegƧg'TheIreferencepGointwithisencircledbyanoutercirclerepresentingtheoriginoftheouterpicture 'environment.jThe@ZinneroriginrepresentedwithanopGencircleisencircledbyanoutercirclecenteredat'theUU(400;240)pGointoftheouterenvironment,resultinginadoublecircle. \ 'SinceweadoptabGondlengthequalto200andabondslopeof(5,t3)or(3,5),suchvqaluesas200,'171, andx103(andanycombinationsofthesevqalues)appGearfrequentlyintypsettingcombinedstructures.'Note2that171isapproximatelyequalto200(5=PpUWPfe E34UY)2and103isaproximatelyequalto200(3=PpUWPfe E34UY).'F*orUUexample,aspirocompGoundcanbetypesetbythestatement:iQ_ObM'CHAPTERUU14.COMBININGSTRUCTURES^d105'fe>|2 '\begin{picture}(1200,900)(0,0) '\put(0,0){\cyclohexanev{}}'\put(342,200){\cyclohexanev{}}'\put(684,0){\cyclohexanev{}}'\end{picture}'TheUUresultingstructuresaree:3ed"~Uɧ"3edb5ɧb3b~Ub3"5"ߟݲPfe}#ݲPfeNe"5"Nebh͟bNPb5ϼbNP"h͟ϼ"5ɲZPfeߟɲZPfeɂed"h͟ɧ"ӂedbڜɧbɂbh͟bӂ"ڜ"iWݲPfe5ݲPfeq|trdred" X>ɧ"redb%ɧbrb X>br"%"/XȟݲPfe % ݲPfe8t@؟Pd6؟e"/"@؟ebGb6؟Pb/ϼb@؟P"Gϼ"QɲZPfe/XȟɲZPfe:tbٔdXٔed"Qɧ"bٔedbirɧbXٔbQbbٔ"ir"s@ݲPfeQݲPfe'TheVright-handstructureistoshowthereferencepGointsandtheinneroriginsofthefragementsused. 'Inuthiscase,2theshiftedvqalues(400;240)ofeachfragmentareequaltothoseofanotherfragment,'since|eachfragmentisgeneratedbythesamemacro.8;Hence,theargumentcoGordinatesofthe\putcan'bGeNcalculatedwithoutconsideringsuchshiftedvqalues.o\Thus,Othevqalue342isequalto1712,and684is'equalUUto1714."'14.2*'CombinationffofMacrosThroughaBondD.'Since2eachofthemacrosdescribGedintheotherchaptersofthepresentmanualisbasedonapicture'environment,Boneofthesimplestwaysofcombiningstructuresistoplaceindividualstructuresintoan'outerUUpictureenvironment.qSuchUUcombinationofmacrosincreasesthevqarietyofstructuraldiagrams. 2 'In@ordertoillustratethemethoGdofcalculatingcoordinates,wetakethedrawingofbiphenylasthe' rstUUexample: '\begin{picture}(1200,600)(0,0)'\put(0,0){\bzdrh{4==}}'\put(546,0){\bzdrh{}}'\end{picture}'ThisUUstatementproGducesthefollowingstructure:G?`5k?`T5(UT`{`TkT`{`(U5fdP5LpfdPɬٟefd-7`KToT`{2fd8``k``T(UT`TkT`(UfdPLpfdPGMefdǫT`T'The rstargumentofeach\putcommandrepresentsthecoGordinatesofthepointonwhichthestructure 'isUUprinted. 'The>(inneroriginofthemacro\bzdrhistheleftmostpGositionofthebenzenering.Thestructuretypeset'bylthecommand\put(0,0){\bzdrh{4==}}hasarightmostterminalpGointat(546;0)withrespGectto'theFUJIT*AUUShinsaku:XMTU>'ExX'fe>|2 'coGordinatesnof\putcanbecalculatedwithoutconsideringsuchshiftedvqalues,(400;240),sinceneachof 'theUUfragmentsisgeneratedbythesamemacro. } 'LetUUusdraw1-chloro-4-morphorinobGenzenebymeansoftwodi erentways.'\begin{picture}(1200,600)(0,0)'\put(0,0){\bzdrh{1==Cl;4==}}'\put(546,0){\sixheteroh[H]{1==N;4==O}{}}'\end{picture}'\qquad'\begin{picture}(1200,600)(0,0)'\put(0,0){\bzdrh{1==Cl;4==N}}'\put(566,0){\sixheteroh[H]{1=={?};4==O}{}}'\end{picture}v'TheseUUstatementsproGduceessentiallythesamestructure:Fu`ygku`Tyg(UT`TgkT`g(UgfdPgLpfdP>efdyMT{ԟT[g1Clgl2fd82fd8P[pT(eTPT^[Tp^(efdPLpfdPO<ۙO5/ۙNq۟`џkq۟`Tџ(UT' `T"!kT' `"!(UџfdPџLpfdPXuefd"ӟ! T r ThClq2fd8<N- 2fd8>rßP@YI[>rßpT@YI(eT\@PTZY[T\@pZY(eFYIfdPFYILpfdP^wۙO'ItNshouldbGenotedthat{4==}inSUBSLISTNproducesabondwithoutasubstituentatthe4-positionof 'theUUbGenzenering,while1=={ }inA*TOMLISTcreatesavqacancytoaccomodatethenitrogenatom. 'The{followingexampleillustratesamorecomplicatedstructurewithaverticalbGondlinkingtwo'fragmentUUstructures.qThus,thestatement'\begin{picture}(1200,1500)(-200,-600)'\put(0,0){\decaheterov[H]{4a==N}{4D==O;7B==HO;{{10}A}==H}}'\put(0,-546){\bzdrv{1==;3==OMe;4==OMe;6==Br}}'\end{picture}v'printsUUthefollowingdiagram:dtb ib7Pfe" i!"dt"ୟ"b`ջb{@feϟdtbୟbϟ"`ջ"ϟdt"Ϭ񟍧"ϟbϬ񟧼!byPfeT~N O!8fe8feeRHOŬ񟍱jbì~7b}HzGЄ̎zGȄ̎zG̎zG̎zG̎zG̎zG̎zG̎ϟ"ϬAw"ϟbୟAwbϟ$bϬVbϟ$"ୟV"{L.PfeyL.Pfe`ղfe-3ebӓgքb-32,"ӓg"8feLbOMeୟL.bݟabݭ)OMe\8feKBrŬKެbìb'The rstargumentofeach\putcommandrepresentsthecoGordinatesofthepointonwhichthestructure 'isprinted. tThevqalue546iscalculatedby140(bGondlength)+406(theheightofthehexagon='103~Q+200+103),׈bGecause~theinneroriginofthestructureprintedby\decaheterovispGosition5(the'leftcarbGonatomadjacenttothenitrogenatom)andthatofthelatterstructureisposition4(thebottom'carbGonUUattachedbythemethoxygroup). 'Thefollowingexampleillustratesacombinedstructureinwhichtwocyclicsubstructuresarelinked'throughUUanaliphaticunitko@ObM'CHAPTERUU14.COMBININGSTRUCTURES^d107'fe>|2 '\begin{picture}(800,1000)(0,0) '\put(0,0){\cyclohexaneh[H]{4==}}'\put(754,0){\bzdrh{1==}}'\put(520,100){\tetrahedral{0==C;1D==O}}'\end{picture}Q7'ThisUUstatementproGduceso_Ə`kƏ`T(UT`˟`T՟kT`˟`՟(UfdPLpfdP`˟2fd8.#` {k.#`T {(UT>_`T:{ikT>_`:{i(U&{fdP&{LpfdP)efd:8/ agT".ST-2fd8gL:CgKO Gs (fe  (fe'Thex4calculationofthevqaluesfor\tetrahedralisslightlycomplicated,sinceitsinneroriginisdi erent 'fromuthoseoftheothercommands./&TherightterminalpGositionduetothe\cyclohexanehisthepoint'(546;0),wthe?x-coGordinateofwhichisequaltothelengthofabenzenering(406)plusabondlength(140).'TheleftterminalpGositionduetothe\bzdrhisthepoint(614;0),because754k140F:=614.VThen,the'aliphaticC unit(\tetrahedral)shouldbGeplacedattheaverageC positionofx-coordinate(546v+614)=2='580.ĄSinceptheinneroriginofthethe\cyclohexanehis(400;240)andthatofthe\tetrahedralis'(300;300),theYx-coGordinateiscalculatedtobe580(300240)=520Ywhilethey[ٲ-coordinateiscalculated'toUUbGe4008300=100.!e'14.3*'UsingffBuildingBlos3cks}'MacrosUU\sixunitvand\fiveunitvaredesignedforbuildinganewfusedringsystem:lI'\sixunitv[BONDLIST]{ATOMLIST}{SUBSLIST}{OMIT}'\fiveunitv[BONDLIST]{ATOMLIST}{SUBSLIST}{OMIT}Q7'whereLargumentOMIT=(a{ffor\sixunitvanda{efor\fiveunitv)isalistofcharacters,$eachofwhich'representsYonebGondtobeomitted.~TheotherargumentshavethesameformatsasdescribGedinthe'preceding~sections.AThesemacrosproGduce ve-andsix-membGeredfragmentsrespGectively*,inwhichthe'bGond:FUJIT*AUUShinsaku:XMTU>'ExX'fe>|2 'isUUtypGesetwiththestatement:P'\begin{picture}(1200,1500)(-200,-600) '\put(0,0){\decaheterov[fhk]{3==N}{6==CH$_3$O;7==CH$_3$O}}'\put(513,-303){\sixunitv[H]{1=={?}}%{3==C$_2$H$_5$;4==CH$_2$COOC$_2$H$_5$}{f}}'\end{picture}<'InUUordertoexaminethedetailsofthecombination,letustypGesetthestructurewiththe rstcommand:D/tϟddtb ib7@fe"[ջ"dt"ୟ"bୟ!b{Pfeϟdtbୟbϟ"ୟ!"ϟdt"Ϭ񟍧"ϟbϬ񟧼!byPfe-3lbӓg<b-3"ӓg'"`fez~NGCH3|sOŬ񟧱"ì"GRCH3|sOŬ񟍱jbì~7b/g'andUUseparatelythestructurewiththesecdondcommand:ɟLVtiKdw\b.GQb$PfeiK".G g" iKb gbYPfe2.{4C2|sH5%.Gb'.w23bßLRCH2|sCOOC2H57L.8fe/g'ItshouldbGenotedthatargumentA*TOMLISTpinthe\sixunitvmacrocontainstheassignment\1=={ }" 'which;assuresthevqacantbridgeheadpGosition.Thisvqacancyisoccupiedbythebridgeheadnitrogenprinted'byUUthe\decaheterovmacro. 8 'The[#followingexamplesillustratecombinationsofdecaheterovand\sixunitvtoproGduceaborane'andUUtherelatedcarbGocycle.P'\begin{picture}(1200,1000)(0,0)'\put(0,0){\decaheterov[H]{}{}}'\put(171,303){\sixunitv[H]{4=={?}}{}{cd}}'\end{picture}'\qquad'\begin{picture}(1200,1000)(0,0)'\put(0,0){\decaheterov[H]{8a==B}{}}'\put(171,303){\sixunitv[H]{4=={?}}{}{cd}}'\end{picture}mObM'CHAPTERUU14.COMBININGSTRUCTURESA109'fe>|2 '\qquad '\begin{picture}(1200,1000)(0,0)'\put(0,0){\sixunitv[H]{2=={?}}{}{a}}'\put(342,0){\sixunitv[H]{}{}{ef}}'\put(171,303){\sixheterovi[H]{1==N}{}}'\end{picture}u'TheseUUstatementsproGducethefollowingstructures.qH_edbfɧbpݲPfe_"f"Ued"N&ɧ"UbN&bNUݲPfe=oHedbD&ɧb=oH"D&"3oHed",Ujɧ"3oHb,Ujb,"8ݲPfeN&bUZb_oҟedPfe=<edPfeD&"=oHZ";edbɧbݲPfe;"";ed"`kǎY";b]bݭ+ݲ<feedb`OǎYb"]"ed"ɧ"bbyoݲPfed0B]b;Zb edPfe̓MedPfe]"Z"mbݲ<fe\"c7"RbK؟bJЦݲPfeRed"K؟ɧ"~QredbkPɧb8ݲPfe~Qr"kP"tQrbm7bm7btQrZbc7"\Z"pǘ"tQ "_ǘb[ꂟQ b~@edPfe[ꄟedPfejʲ^B'ThecsecondandthirdexamplesabGovecshowalternativewaystodepictthecarbGorane.fNotethatthe 'argumentUU{2=={ }}inthethirdexampleisnecessarytoprintthedesiredstructures. | 'TheUUfollowingtwoexmaplesinvolveacombinationoftwo\sixunitvcommands.'\begin{picture}(1200,800)(0,0)'\put(0,0){\sixunitv[H]{3==O}{1D==O;4==CH$_{3}$}{b}}'\put(342,0){\sixunitv[H]{5=={?}}{4D==O}{e}}'\end{picture}'\qquad'\begin{picture}(1200,800)(0,0)'\put(0,0){\sixunitv[c]{}{}{b}}'\put(342,0){\sixunitv[a]{}{}{e}}'\end{picture}u'TheseUUstatementsprovide]edb4Ÿɧb"֫"{btbsԟݲPfe{ed"tɧ"O>Ozed8feꟿed8fe>CH3粟؄8feNedbh~ɧb5LݲPfeN"h~"NbП֫bNed"4Ÿɧ"4O6؄8feN؄8feredbɧbr"" rbX=b% ݲPfe red"X=ɧ" \"="6ןedb=ɧbGݲPfe6ן"=",ןb%b,ןed"%ɧ"7?sɘb9?(b 'Thefollowingexmapleinvolvesacombinationofthree\sixunitvcommandsandone\bzdrvcom- 'mand.'\begin{picture}(1600,800)(0,0)'\put(0,0){\bzdrv[r]{1==OH;5==THPO}}'\put(342,0){\sixunitv[c]{2==O}{1D==O}{be}}'\put(684,0){\sixunitv[H]{6=={?}}{1==CH$_{3}$}{be}}'\put(1026,0){\sixunitv[H]{}{3D==O}{e}}'\end{picture}u'ThisUUstatementprovidesnObM'110>FUJIT*AUUShinsaku:XMTU>'ExX'fe>|2 /ed"Qɧ"/edb ɧb/bQb/" "ɬ۟ݲPfeyݲPfe`fe,\bǟ=b,ɘ"ǟ("OHed8fe}]THPOQ㲪"!"edbޓǎYb"ɟ"b bed" ɧ"ۓ\"-S="z!0OEOٓed8feed8fe-edbGɧb-"G"-bɟb-ed"ןǎY"CH3ued8feacedb&{Aɧb0HݲPfeac"&{A"acbGbaced"Gɧ"={u޲O0.seb2.b0b2? b 'AUUbicyclo[3.3.1]nonaneistypGesetbythistechnique.'\begin{picture}(1600,800)(0,0) '\put(0,0){\cyclohexaneh[H]{3Sa==\lmoiety{H$_{5}$C$_{2}$OCO\kern2em}}}'\put(200,0){\sixunith[H]{}{3D==O;4==CO$_{2}$C$_{2}$H$_{5}$}{af}}'\end{picture}'\qquad'\begin{picture}(1600,800)(0,0)'\put(0,0){\cyclohexaneh[H]{3Sa==\lmoiety{H$_{5}$C$_{2}$OCO\kern2em}}}'\put(200,0){\fiveunith[H]{}{2D==O;1==CO$_{2}$C$_{2}$H$_{5}$}{c}}'\end{picture}'TheseUUstatementsprovideequivqalentresultsasfollows.ZM`QfkM`TQf(UTo@`TkgJkTo@`kgJ(UWffdPWfLpfdPH*˟BH5|sC2OCOk4傄8fekgJfdP`TgkT`g(UkgJLpfdPgBOП2PN 2P},Ƙ~|ĘhCO2|sC2H52fd8q۟`џkq۟`Tџ(UT' `T"!kT' `"!(UџfdPџLpfdPBH5|sC2OCO"傄8fe; g`T6qkT"!fdP"!LpfdP; g`6q(U|2 '\put(342,0){\sixunitv[H]{6=={?}}{}{ef}} '\put(171,303){\pyridinevi{}}'\end{picture}'\qquad'\begin{picture}(1200,1000)(0,0)'\put(0,0){\sixunitv[H]{2=={?}}{}{ab}}'\put(342,0){\fiveunitvi[H]{5=={?}}{}{de}}'\put(171,303){\pyridinevi{}}'\end{picture}'\qquad'\begin{picture}(1200,1000)(0,0)'\put(0,0){\sixunitv[H]{2=={?}}{}{ab}}'\put(342,0){\sixunitv[H]{6=={?}}{}{ef}}'\put(171,303){\bzdrv{4Sa==\kern.5em\raise1ex\hbox{Br}}}'\end{picture}'TheseUUstatementsprovidenWyp8""op8bhVZbh#(ݲPfeop8ed"hVZɧ"edbҟɧbݲPfe"ҟ"bbbZb"yp8Z" $ǘ"(Q "} ǘby=Q bpŸedPfey=edPfe} b} bzKb"}Vھ"#蟼feppʲ^Nϟ"ୟ"ϟbϬbyݲPfeϟed"Ϭɧ"edb iɧb7ݲPfeୟ܄fd"3ୟbZbୟ"ϟZ"`ǘ"-Q "`ǘbQ bYedPfeedPfe`b`wbGKb"Eھ"zfeʲ^NHf"O7D">fb7b6VݲPfe>fed"7ɧ"jQ"edbqkɧb{7ΟݲPfejQ""qk"`Q"bY7DbO7D"HfZ"Y7Db`Q"ZbO7DɲZbHfobY7DɲZ"`Q"o"jedPfeG4edPfeffeNbLܟbNKb"Lܟھ"bPd~BrY7DӲZTZjղZT 'W*ehaverepGortedanarticleondyereleasersforinstantcolorphotography*,inwhichavqarietyof 'structuralC}formulashavebGeentypGesetbymeansoforiginalutilitiesoftheL5ffA͉TU>'ExXpictureenvironment'[10 ].kThe#presentXMTU>'ExXprovidesuswithamoreversatiletoGolofdrawingsuchcomplexmolecules.'Thus,UUtheformulaofacyandyereleaserforinstantcolorphotographyistypGesetbythestatement:'\begin{picture}(4000,2000)(0,-1000)'\put(0,0){\bzdrv{1==OH;2==NH--SO$_{2}$;4==OC$_{16}$H$_{33}$;5==CH$_{3}$}}'\put(993,230){\bzdrh{1==;2==OCH$_{2}$CH$_{2}$OCH$_{3}$;%'5==NH--SO$_{2}$}}'\put(1890,-140){\bzdrh{1==;5==SO$_{2}$--NH}}'\put(2750,-850){\naphdrh{1==;5==OH;8==}}'\put(1800,-850){\bzdrh{1==O$_{2}$N;5==SO$_{3}$CH$_{3}$;4==N=N}}'\end{picture}'%}pؠObM'112=FUJIT*AUUShinsaku:qXMTU>'ExX'fe>|2  'TheseUUcommandsproGducethefollowingstructure:獍6OacԬ"/qec"@OacbG-ecb6Ob/qb@O"G-"QyPfe/w?yPfeN^!wvfe6*b3~;pb6*e"3g&t"=KbOH@[cԄ8fe^a_NH{SO2Q-eʬ"S]d}"=lOC16xH33@H8fet埆NCH3%q"#AM"i\t__UiftT__n&iT\tT_UTft_n&i__LȄfdP__nJfdPOcfdyagujEgTjT1]0fd8_+;VOCH2|sCH2OCH3__K㖬T,IT_ǟ1HNH{SO2_xRTzRTzT&Ta?T IzTa? I&q\fdPKfdPtd6fd - aGT3T˟1:fd8a1ܲSO2|s{NH IT GTC[$HQ/C[$THQ(Tfb$Tb/Tfb$b(NQxfdPNQL4fdPC[hHQsC[hTHQ]TfbhTbsTfbhb]NQ伄fdPG1Iȋ1b/S1T`bg1Tb/SӘ`bg֘GӘTIȋ֘TPeRfd5#2Vfd8| ʲOHlb2Vfd85#fd8ߟ$՟/ߟ$T՟(Ta$T%/Ta$%(՟xfdP՟L4fdPyeRfd-ןӘ`֘#ӘT֘TO۟ʲO2|sNƧ2Vfd8 =2SO3|sCH3%TGuTʲN=N a2Vfd8qObM2Ŵ'UChapter 153'TLarge T{Substituen8ts;'15.1*'BasicffIdeas 'Intalloftheprecedingchapters,|anytsubstituentsdescribGedinSUBSLISTtarerathersimpleones,|which 'atj?mostvqaryfromanatomofone-ortwo-characterj?toagroupofseveralcharacters.HowabGoutsucha'complexUUsubstituentasproGducedbyamacro? 'LetUUusconsiderthesubstitutionofgݍϟed"Ϭɧ"ϟedbୟɧbϟbϬbϟ"ୟ"{ݲPfeyݲPfe`fe-3\bӓg=b-3ɘ"ӓg("ݭ)OHed8feòBୟɲZ"ݟ'"ݭ)OC16xH33؄8fewe޲CH3Ŭ㲪"ì"2ލ'atUUthe2-pGosition()withthesubstituentrepresentedbybo`uk`Tu(UT``TşkT``ş(UufdPuLpfdP٭efd-w`ßTƯTA?NH{SO2G2fd8ABOCH2|sCH2OCH3u催T%Tݞ34NO2ş>TG>T'ThistaskcanbGeaccomplishedinthelightofthetechniqueintroGducedintheprecedingchapter. Thus, 'theUUstatement}'\begin{picture}(2000,1000)(0,0)'\put(0,0){\bzdrv{1==OH;2==;4==OC$_{16}$H$_{33}$;5==CH$_{3}$}}'\put(993,230){\bzdrh{1==NH--SO$_{2}$;%'2==OCH$_{2}$CH$_{2}$OCH$_{3}$;5==NO$_{2}$}}'\end{picture}2ލ'providesKF113r͠ObM'114=FUJIT*AUUShinsaku:qXMTU>'ExX'fe>|2 ߟed"ɧ"ߟedb߽ɧbߟbbߟ"߽"ݲPfexϟݲPfe_fe,C\bw=b,Cɘ"w("9OHed8fe߽ɲZ"'"9OC16xH33؄8fesvu޲CH3㲪"џ"`T`'T5Ta?T5a?'`XfdP`LfdPe2fdz˘ΘG=˘T)ΘTŽNH{SO226fd8`OCH2|sCH2OCH3`&T-&TaW2زNO2a?TT7'ThisUUmethoGdologyimpliesthatbothofthepartsareregardedasfragmentstobecombinedtogether.  'Onrtheotherhand,yanotherusefultechniqueisavqailable,yifyouusetheTU>'ExXcommand\setboxand 'the [relatedcommands.YInthelightofthistechnique,&eitheroneisregardedasasubstituentoftheother.'First,astructureregardedasasubstituentisconstructedina\hboxandstoredin\box4bymeansof'theUUcommand\setboxasfollows:J'\setbox4=\hbox{%g\begin{picture}(0,0)(-285,370)%'% \put(-285,370){\circle{50}}%change?referencepoint\put(0,0){\bzdrh{1==NH--SO$_{2}$;2==OCH$_{2}$CH$_{2}$OCH$_{3}$;% 5==NO$_{2}$}}%g\end{picture}}%'Theinnerpictureenvironmenthasthewidthof0ptandtheheightof0pt,EwherethereferencepGointis'shifted5;intothe(285;370)pGointwhichistherightmostpGointoftheNH{SO2group.yThisreference'pGointisregaredasthe(0;0)pointofthesubstituentstoredin\box4.NThen,thesubstituent\box4is'writtenUUinSUBSLISTofthecommand\bzdrv,i.e.,J'\bzdrv{1==OH;2==\box4;4==OC$_{16}$H$_{33}$;5==CH$_{3}$}'ThisUUstatementproGduceso=ߟed"ɧ"ߟedb߽ɧbߟbbߟ"߽"ݲPfexϟݲPfe_fe,C\bw=b,Cɘ"w("9OHed8fe`ß6A`ßʲ6T+T6T ATʲ6 +ˊfdPFfdPG]dfdǻKϟKKT`KTۃܲNH{SO2`hfd8OCH2|sCH2OCH3XTziXT! NO2 TYT߽ɲZ"'"9OC16xH33؄8fesvu޲CH3㲪"џ"'ItshouldbGenotedthatthetoken2==\box4createssuchacomplexfragmentthatisimpGossibleto'bGedirectlyassignedtoanargumentlist.JbThistechniqueisalsousefultoavoidtheovercrowdingof'substituents,UUsincethereferencepGointofthesubstituentcanbGechangedappropriately*.  'Whenyoumultipletimesusethestoredsubstituent,Pyoucanusethecommand\copyinsteadof\box:J'\bzdrv{1==OH;2==\copy4;4==OC$_{16}$H$_{33}$;5==CH$_{3}$}'Then,UUyouareabletousethestoredsubstituentinanothercontext.'\setbox5=\hbox{% '\bzdrv{1==OH;2==\box4;5==C$_{16}$H$_{33}$O;4==CH$_{3}$}}%'\mbox{\box5}'ThisUUstatementprovidesanotherderivqativehavingthesamesubstituents.s$ObM'CHAPTERUU15.LARGESUBSTITUENTS115'fe>|2 ߟed"ɧ"ߟedb߽ɧbߟbbߟ"߽"ݲPfexϟݲPfe_fe,C\bw=b,Cɘ"w("9OHed8fe`ß6A`ßʲ6T+T6T ATʲ6 +ˊfdPFfdPG]dfdǻKϟKKT`KTۃܲNH{SO2`hfd8OCH2|sCH2OCH3XTziXT! NO2 TYT߽ɲZ"'"_9޲C16xH33O㲪"џ"9CH3؄8fe ɍ'15.2*'NestedffSubstituents'TheJlastestsamplerevealsthatastructureconstructedbythepresenttechiquecanbGefurthernestedto 'bGeasubstituentofanothermacro.VThefollowingexampleillustratesmultiplenestingfordrawingthe'sameUUdyereleaserasdepictedintheprecedingchapter. 'First,wtheaformulaof2-methanesulfonyl-4-nitro-phenyl-1-azogroup(A)aisconstructedinthebGox\box4'byUUmeansoffollowingstatement:6'\setbox4=\hbox{%g\begin{picture}(0,0)(996,370)%'% \put(996,370){\circle{50}}%\put(0,0){\bzdrh{1==O$_{2}$N;5==SO$_{3}$CH$_{3}$;4==N=N}}%g\end{picture}}%'Note.thatthevqalue(996,370)shiftsthereferencepGointintotherightmostterminaloftheazogroup,'which%isalinkingpGointinthenextstep.aTheformula(A)%stroredin\box4isplacedatthe8-pGositionof'aUUnaphalenering.qTheresultingformula(B)is,inturn,storedinto\box5.'\setbox5=\hbox{%g\begin{picture}(0,0)(-250,712)%'% \put(-250,712){\circle{50}}%\put(0,0){\naphdrh{1==SO$_{2}$NH;5==OH;8==\box4}}%g\end{picture}%g}%'TheZvqalue(250;712)shiftsthereferencepGointintotheleftmostterminalofthesulfonamidogroupat'thed1-pGositionofthenaphthalenering.TheformulaBdanasulfamoylgroupareplacedatthemeta'pGositionUUofabenzenringtoproduceformulaC.'\setbox4=\hbox{%g\begin{picture}(0,0)(-285,370)%'% \put(-285,370){\circle{50}}%\put(0,0){\bzdrh{1==NH--SO$_{2}$;5==\box5}}%g\end{picture}%'}%'TheresultingformulaCisfurtherplacedonanotherbGenzeneringtogeneratetheformula(D)ofa'complexUUsubstituent.'\setbox5=\hbox{%g\begin{picture}(0,0)(-285,370)%'% \put(-285,370){\circle{50}}%\put(0,0){\bzdrh{1==NH--SO$_{2}$;2==OCH$_{2}$CH$_{2}$OCH$_{3}$;% 5==\box4}}%g\end{picture}%'}%tObM'116=FUJIT*AUUShinsaku:qXMTU>'ExX'fe>|2 'Finally*,UUthesubstituentDisplacedattheorthopGositiontoahydroxylgrouponabGenzenering.'\setbox4=\hbox{% '\bzdrv{1==OH;2==\box5;4==OC$_{16}$H$_{33}$;5==CH$_{3}$}}%'\mbox{\box4}dN'TheJnformulastoredin\box4isprintedbymeansofthecommand\box4,Lgivingthefollowingstructure.󍍍6OacԬ"/qec"@OacbG-ecb6Ob/qb@O"G-"QyPfe/w?yPfeN^!wvfe6*b3~;pb6*e"3g&t"=KbOH@[cԄ8fe_3\)U_3fT)mٛTo\TyUTofymٛ)KfdP)mfdPE͠OԄfd+gJB?jJBwgJBT_cjJBT]_LNH{SO2^\؄fd8;OCH2|sCH2OCH3)KȬTx٠IT-cnzYzy-cnTzY cTǟnT zzyTǟn z czYp„fdPzY1~fdPtJfd [~ o~ `~ T-~ T#NH{SO2-+fd8A{KE{"A{KTE{tTdKT_˟"TdK_˟tK{eFfdPK{ڙfdPA{6E{AA{6TE{A+Td6T_˟ATd6_˟A+K{1fdPEɟ~G{~_}~T^~T_}^EɟTG{TNb fd-KezA<-KeTzAڎTLJeTz|2 '%} '\end{center}'TheseUUcommandsproGducekd"{"kdbI{bk(bżbk("Iż"ح2Pfey[2Pfe'd"I{"'db{b'(bIżb'("ż"ӟ2PfedPfe"'Z5"b-㟍Z5b dPfe"-㟧oS"G" -㟍Z5"Gb$aZ5b..mdPfe -㟡fd"3txQٲzxQϲzxϲx|fd3YٲTӲTtxQ㲚TzxQTzxT))YxP3ɲZOy'ٲ fey̲fOy' feyHx fexಶHx fex6OHEO fe}EAಶHEO fe}EA6OHtEٲ fehdr̲fHOtE fep+HEOŲJ fe}EAHEOF fe}EAزCH3Ų2"]e";aӟdOH.ad"0aϟ1i"Gun"$ap"Gunb -pb..mjx<fe jxPfe -VZfdx%p*bYoTb*YOfPOzVbzTbXbW}cb8feyҟpHCOح8fe =eHOH e$8fe}*H3|sC d8fev ObM'118=FUJIT*AUUShinsaku:qXMTU>'ExX'fe>|2w<ObM2 'TBibliograph8y5Vw'[1]KnuthUUD.,TheTKß'E-Xb}'ook,UUAddison-W*esley,Reading(1984).'[2]Ito*T.,Kagaku͵toKo}'gyo,46,66*(1993).ThisarticledescribGedthattheChemicalSocietyofJapan changedS)thepublishingproGcessofitsjournal(Bull.Chem.So}'c.Jpn.)S)onJanuary1993intotheonethatUUisbasedonthecombinationofTU>'ExXandSGML(StandardGeneralizedMark-upLanguage).'[3]LampGortUUL.,L雍Qt}\cmti7ATKß'E-XAdo}'cumentPreparationSystem,UUAddison-W*esley,Reading(1986).'[4]HaasUUR.T.&O'KaneK.C.,Comput.Chem.,11,251(1987).'[5]Ramek,PM.,inClark,M.(ed),TU>'ExX:cYApplications,Uses,MethoGds,EllisHorwoGod,PLondon(1990),p.UU277.'[6]F*ujita%S.,\TypGesettingstructuralformulaswiththetextformatterTU>'ExX/L5ffA͉TU>'EX",Comput.Chem.,inUUpress.'[7]F*ujitaS.,Kagakusha-SeikagakushaUnotamenoL雍QATKß'E-X(L雍QATKß'E-XforChemistsandBio}'chemists),T*okyoKagakuUUDozin,T*okyo(1993).'[8]PoGdarZS.,[\EnhancementstothepictureenvironmentofL5ffA͉TU>'ExX",[ManualforV*ersion1.2datedJuly14,UU1986.'[9]F*ujitaS.,\PromoleculeswithsubsymmetryofD1h 'l.CombinatorialenumerationandstereoGchemicalpropGerties",UUJ.Chem.Inf.Comput.Sci.,32,354{363(1992).'[10]F*ujitaS.,.KoyamaK.,.&OnoS.,\Dyereleasersforinstantcolorphotography",.R}'ev.3jHeteroatomChem.,UU7,229{267(1992).KF119xObM'120hP5BIBLIOGRAPHY'fe>|2y ObM2#y'UAppendix A2d'TList T{ofCommands:d'A.1&0aliphat.sty\'TheUUstyle le`aliphat.sty'containsthefollowingcommands~'% '% '%'%?\tetrahedralx\@tetrahedral'%?\square\@square'%'% '%'%?\rtrigonal?\@rtrigonal'%?\ltrigonal?\@ltrigonal'%?\utrigonal?\@utrigonal'%?\Utrigonal?\@Utrigonal'%?\dtrigonal?\@dtrigonal'%?\Dtrigonal?\@Dtrigonal'%'% '%'%?\ethylene\@ethylene'%?\ethylenev?\@ethylenev'%?\Ethylenev?\@Ethylenev'%'% '%'%?\tetrastereox\@tetrastereo'%?\dtetrastereos\@dtetrastereo'%?\ethanestereos\@ethanestereo'%!|'A.2&0carom.sty'TheUUstyle le`carom.sty'containsthefollowingcommands.e'%KFβ121z ObM'122>FUJIT*AUUShinsaku:XMTU>'ExX'fe>|2 '% '%'%?\cyclohexanevN\@cyclohexanev'%?\bzdrvs\@bzdrv'%?\decalinev^\@decalinev'%?\naphdrvh\@naphdrv'%?\tetralinevY?\@tetralinev'%?\hanthracenevN\@hanthracenev'%?\anthracenevS\@anthracenev'%?\hphenanthrenevD?\@hphenanthrenev'%?\phenanthrenevI\@phenanthrenev'%?\steroidh\@steroid'%?\steroidchainN\@steroidchain'%'%'%'%?\cyclohexanehN\@cyclohexaneh'%?\bzdrhs\@bzdrh'%?\decalineh^\@decalineh'%?\naphdrhh\@naphdrh'%?\tetralinehY?\@tetralineh'%"d'A.3&0lowcycle.styʍ'TheUUstyle le`lowcycle.sty'containsthefollowingcommands.'%'%?\cyclopentanevs\@cyclopentanev'%?\cyclopentanevin?\@cyclopentanevi'%?\cyclopentanehs\@cyclopentaneh'%?\cyclopentanehin?\@cyclopentanehi'%?\indanev\@indanev'%?\indanevi\@indanevi'%?\indaneh\@indaneh'%?\indanehi\@indanehi'%?\cyclobutane}\@cyclobutane'%?\cyclopropanex\@cyclopropane'%'%'A.4&0ccycle.styʍ'TheUUstyle le`ccycle.sty'containsthefollowingcommands._͍'%'% '%'%?\chairn?\@chair'%?\bicychepvY?\@bicychepv'%?\bicychephY?\@bicycheph{ObM'APPENDIXUUA.LISTOFCOMMANDS123'fe>|2 '%?\bornanec\@bornane '%?\adamantaneS\@damantane'%!'A.5&0hetarom.styG'TheUUstyle le`hetarom.sty'containsthefollowingcommands.Z'%'% '%Basic?Macros'%'%?\sixheterovN\@sixheterov'%?\sixheteroviI\@sixheterovi'%'%Application?Macros'%'%?\pyridinevS\@pyridinev'%?\pyridineviN\@pyridinevi'%?\pyrazinevS\@pyrazinev'%?\pyrimidinevI\@pyrimidinev'%?\pyrimidineviD?\@pyrimidinevi'%?\pyridazinevI\@pyridazinev'%?\pyridazineviD?\@pyridazinevi'%?\triazinevS\@triazinev'%?\triazineviN\@triazinevi'%'% '%Basic?Macros'%'%?\fiveheterovI\@fiveheterov'%?\fiveheteroviD?\@fiveheterovi'%'%Application?Macros'%'%?\pyrrolevY?\@pyrrolev'%?\pyrazolevS\@pyrazolev'%?\imidazolevN\@imidazolev'%?\isoxazolevN\@isoxazolev'%?\oxazolevY?\@oxazolev'%?\pyrroleviS\@pyrrolevi'%?\pyrazoleviN\@pyrazolevi'%?\imidazoleviI\@imidazolevi'%?\isoxazoleviI\@isoxazolevi'%?\oxazoleviS\@oxazolevi'%'% '%Basic?Macros'%'%?\decaheterovI\@decaheterov'%?\decaheteroviD?\@decaheterovi|ObM'124=FUJIT*AUUShinsaku:qXMTU>'ExX'fe>|2 '% 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'%'%?\sixunitvY?\@sixunitv'%?\fiveunitvS\@fiveunitv'%?\fiveunitviN\@fiveunitvi'%}SObM'APPENDIXUUA.LISTOFCOMMANDS125'fe>|2 'A.6&0hetaromh.sty'TheUUstyle le`hetaromh.sty'containsthefollowingcommands.Ѝ'% '% '%'%Basic?Macros'%'%?\sixheterohS\@sixheteroh'%?\sixheterohiN\@sixheterohi'%'%Application?Macros'%'%?\pyridinehY?\@pyridineh'%?\pyridinehiS\@pyridinehi'%?\pyrazinehY?\@pyrazineh'%?\pyrimidinehN\@pyrimidineh'%?\pyrimidinehiI\@pyrimidinehi'%?\pyridazinehN\@pyridazineh'%?\pyridazinehiI\@pyridazinehi'%?\triazinehY?\@triazineh'%?\triazinehiS\@triazinehi'%'% '%'%Basic?Macros'%'%?\fiveheterohN\@fiveheteroh'%?\fiveheterohiI\@fiveheterohi'%'%Application?Macros'%'%?\pyrroleh^\@pyrroleh'%?\pyrazolehY?\@pyrazoleh'%?\imidazolehS\@imidazoleh'%?\isoxazolehS\@isoxazoleh'%?\oxazoleh^\@oxazoleh'%?\pyrrolehiY?\@pyrrolehi'%?\pyrazolehiS\@pyrazolehi'%?\imidazolehiN\@imidazolehi'%?\isoxazolehiN\@isoxazolehi'%?\oxazolehiY?\@oxazolehi'%'% '%'%Basic?Macros'%'%?\decaheterohN\@decaheteroh'%?\decaheterohiI\@decaheterohi'%'%Application?Macros'%~#ObM'126>FUJIT*AUUShinsaku:XMTU>'ExX'fe>|2 '%?\quinolinehS\@quinolineh '%?\quinolinehiN\@quinolinehi'%?\isoquinolinehD?\@isoquinolineh'%?\isoquinolinehi>\@isoquinolinehi'%?\quinoxalinehI\@quinoxalineh'%?\quinazolinehI\@quinazolineh'%?\quinazolinehiD?\@quinazolinehi'%?\cinnolinehS\@cinnolineh'%?\cinnolinehiN\@cinnolinehi'%?\pteridinehS\@pteridineh'%?\pteridinehiN\@pteridinehi'%'% '%'%Basic?Macros'%'%?\nonaheterohN\@nonaheteroh'%?\nonaheterohiI\@nonaheterohi'%'%Application?Macros'%'%?\purinehc\@purineh'%?\purinehi^\@purinehi'%?\indolehc\@indoleh'%?\indolehi^\@indolehi'%?\indolizinehN\@indolizineh'%?\indolizinehiI\@indolizinehi'%?\isoindolehS\@isoindoleh'%?\isoindolehiN\@isoindolehi'%?\benzofuranehI\@benzofuraneh'%?\benzofuranehiD?\@benzofuranehi'%?\isobenzofuraneh9\@isobenzofuraneh'%?\isobenzofuranehi4\@isobenzofuranehi'%?\benzoxazolehI\@benzoxazoleh'%?\benzoxazolehiD?\@benzoxazolehi'%'%'%'%?\sixunith^\@sixunith'%?\fiveunithY?\@fiveunith'%?\fiveunithiS\@fiveunithi'%!'A.7&0hcycle.styG'TheUUstyle le`hcycle.sty'containsthefollowingcommands.Z'%'%?'%'%?\pyranoseY?\@pyranose'%?\furanoseY?\@furanose*DObM'APPENDIXUUA.LISTOFCOMMANDS127'fe>|2 '%!č'A.8&0chemstr.sty'TheUUstyle le`chemstr.sty'containsthefollowingcommands.'% '% 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