高等有机化学:反应与合成：第5版

Preface

AcknowledgmentandPersonalStatement

Introduction

Chapter1.AlkylationofEnolatesandOtherCarbonNucleophiles

Introduction

1.1.GenerationandPropertiesofEnolatesandOtherStabilizedCarbanions

1.1.1.GenerationofEnolatesbyDeprotonation

1.1.2.RegioselectivityandStereoselectivityinEnolateFormationfromKetonesandEsters

1.1.3.OtherMeansofGeneratingEnolates

1.1.4.SolventEffectsonEnolateStructureandReactivity

1.2.AlkylationofEnolates

1.2.1.AlkylationofHighlyStabilizedEnolates

1.2.2.AlkylationofKetoneEnolates

1.2.3.AlkylationofAldehydes,Esters,CarboxylicAcids,Amides,andNitriles

1.2.4.GenerationandAlkylationofDianions

1.2.5.IntramolecularAlkylationofEnolates

1.2.6.ControlofEnantioselectivityinAlkylationReac:ions

1.3.TheNitrogenAnalogsofEnolsandEnolates:EnaminesandImineAnions

GeneralReferences

Problems

Chapter2.ReactionsofCarbonNucleophileswithCarbonylCompounds

Introduction

2.1.AldolAdditionandCondensationReactions

2.1.1.TheGeneralMechanism

2.1.2.ControlofRegio-andStereoselectivityofAldolReactionsofAldehydesandKetones

2.1.3.AldolAdditionReactionsofEnolatesofEstersandOtherCarbonylDerivatives

2.1.4.TheMukaiyamaAldolReaction

2.1.5.ControlofFacialSelectivityinAldolandMukaiyamaAldolReactions

2.1.6.IntramolecularAldolReactionsandtheRobinsonAnnulation

2.2.AdditionReactionsofIminesandIminiumIons

2.2.1.TheMannichReaction

2.2.2.AdditionstoN-AcylIminiumIons

2.2.3.Amine-CatalyzedCondensationReactions

2.3.AcylationofCarbonNucleophiles

2.3.1.ClaisenandDieckmannCondensationReactions

2.3.2.AcylationofEnolatesandOtherCarbonNucleophiles

2.4.OlefinationReactionsofStabilizedCarbonNucleophiles

2.4.1.TheWittigandRelatedReactionsofPhosphorus-StabilizedCarbonNucleophiles

2.4.2.Reactionsofa-TrimethyisilylcarbanionswithCarbonylCompounds

2.4.3.TheJuliaOlefinationReaction

2.5.ReactionsProceedingbyAddition-Cyclization

2.5.1.SulfurYiidesandRelatedNucleophiles

2.5.2.NucleophilicAddition-Cyclizationofot-Haloesters

2.6.ConjugateAdditionbyCarbonNucleophiles

2.6.1.ConjugateAdditionofEnolates

2.6.2.ConjugateAdditionwithTandemAlkylation

2.6.3.ConjugateAdditionbyEnolateEquivalents

2.6.4.ControlofFacialSelectivityinConjugateAdditionReactions

2.6.5.ConjugateAdditionofOrganometallicReagents

2.6.6.ConjugateAdditionofCyanideIon

GeneralReferences

Problems

Chapter3.FunctionalGroupInterconversionbySubstitution,IncludingProtectionandDeprotection

Chapter4.ElectrophilicAdditionstoCarbon-CarbonMultipleBonds

Chapter5.ReductionofCarbon-CarbonMultipleBonds,CarbonylCroups,andOtherFunctionalGroups

Chapter6.ConcertedCycloadditions,UnimolecularRearrangements,andThermalEliminations

Chapter7.OrganometallicCompoundsofGroupIandIIMetals

Chapter8.ReactionsInvolvingTransitionMetals

Chapter9.Carbon-CarbonBond-FormingReactionsofCompoundsofBoron,Silcon,andTin

Chapter10.ReactionsInvolvingCarbocations,Carbenes,andRadicalsandReactiveIntermediates

Chapter11.AromaticSubstitutionReactions

Chapter12.Oxidations

Chapter13.MultistepSyntheses

References

Index

　　Thecontrolofreactivitytoachievespecificsynthesesisoneoftheoverarchinggoalsoforganicchemistry.Inthedecadesincethepublicationofthethirdedition,majoradvanceshavebeenmadeinthedevelopmentofefficientnewmethods,particularlycatalyticprocesses,andinmeansforcontrolofreactionstereochemistry.Thisvolumeassumesaleveloffamiliaritywithstructuralandmechanisticconceptscomparabletothatinthecompanionvolume,PartA,StructuresandMechanisms.Together,thetwovolumesareintendedtoprovidetheadvancedundergraduateorbeginninggraduatestudentinchemistrywithasufficientfoundationtocomprehendandusetheresearchliteratureinorganicchemistry.　　自从1977年面世以来，《高等有机化学》作为学科首选教材的地位一直没有动摇过，广泛地覆盖了有机化合物的结构、反应活性及合成。她的第五版相对2001年出版的第四版进行了大幅度的修订，更新了学科发展的相关资料，内容组织更加清晰明朗，特别是计算化学部分。通过控制反应而得到特定的合成是有机合成的全部目标。PartB在不同反应类型的基础上详尽地描述了最常见的和最有用的合成反应。每章后附有习题精选及解答习题的推荐参考文献。　　本书可供有机化学、药物化学和生物化学等专业的高年级本科生、研究生以及相关领域的科研人员参考。