农药的有机合成讲义

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1、OrganicSynthesisConcepts,Methods,StartingMaterialsSecond,RevisedandEnlargedEditionVCHWeinheim•NewYorkBasel•Cambridge•TokyoProf.Dr.JϋrgenFuhrhopAbbreviations1SynthonsintheSynthesisofCarbonChainsandCarbocyclesIntroductionendSummary2SelectiveFunctionalGroupInterconversions(FG

2、I)3Retro-SyntheticAnalysisofSimpleOrganicCompounds4MethodsintheConstructionofComplexMolecules5ConceptsinNanometerSizeArchitecture1SynthonsintheSynthesisofCarbonChainsandCarbocyclesMostsyntheticreactions,whichproducecarbon-carbonbonds,arepolar:anegativelypolarized("electron

3、egative")carbonatom(electrondonor,d)ofonereagentiscom-combinedwithapositivelypolarized("electropositive")carbonatom(electronacceptor,a)ofanotherreagent.Anewcovalentcarbon-carbonbondisformed.Theformalcarbanionsandcarbocationsusedasunitsinsynthesisarecalleddonorsynthonsandac

4、ceptorsynthons.Theyarederivedfromreagentswithfunctionalgroups.Example:CH3-methyldonorsynthon(fromthereagentCH3Li)СH3+methylacceptorsynthon(fromthereagentCH3I)Thecombination(=syntheticreaction)ofbothsynthonswouldyieldethane.Thechangeofadonorreagentintoanacceptorreagentandvi

5、ceversaiscalled"um-polung"(=dipoleinversion).Example:(a)(d)CH3I+2Li.→CH3Li+Lil•Synthonsarenumberedaccordingtotherelativepositionsofafunctionalgroup(FG)andthereactivecarbonatom.•Synthonsarenumberedaccordingtotherelativepositionsofafunctionalgroup(FG)andthereactivecarbonatom

6、.X=heteroatomFG=functionalgroupFGIfthecarbonatomC-lofthefunctionalgroupitselfisreacting,onehasad1-ora1-synthon.IfthecarbonatomC-2nexttothefunctionalgroup(thea-carbonatom)isthereactioncentre,wecallitad2-ora2-synthon.Iftheβ-carbonatomC-3isthereactiveone,weassignd3ora3totheco

7、rrespondingsynthon,etc.Alkylsynthonswithoutfunctionalgroupsarecalledalkylatingsynthons.Theelectronegativeheteroatomofthefunctionalgroupmayalsoformcovalentbondswithacceptorsynthons.Insuchcaseswespeakofd0synthons.Thecombinationoftworeagentscorrespondingtooned-synthonandonea-

8、synthonunderappropriateconditionsyieldsanadditionalcarbon-carbonbond(exception:d°-synthon