The control of reactivity to achieve specific syntheses is one of the overarching goals of organic chemistry. In the decade since the publication of the third edition, major advances have been made in the development of efficient new methods, particularly catalytic processes, and in means for control of reaction stereochemistry. This volume assumes a level of familiarity with structural and mechanistic concepts comparable to that in the companion volume, Part A, Structures and Mechanisms. Together, the two volumes are intended to provide the advanced undergraduate or beginning graduate student in chemistry with a sufficient foundation to comprehend and use the research literature in organic chemistry.

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。Part B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。

Preface

Acknowledgment and Personal Statement

Introduction

Chapter 1. Alkylation of Enolates and Other Carbon Nucleophiles

Introduction

 1.1. Generation and Properties of Enolates and Other Stabilized Carbanions

1.1.1. Generation of Enolates by Deprotonation

1.1.2. Regioselectivity and Stereoselectivity in Enolate Formation from Ketones and Esters

1.1.3. Other Means of Generating Enolates

1.1.4. Solvent Effects on Enolate Structure and Reactivity

 1.2. Alkylation of Enolates

1.2.1. Alkylation of Highly Stabilized Enolates

1.2.2. Alkylation of Ketone Enolates

1.2.3. Alkylation of Aldehydes, Esters, Carboxylic Acids, Amides, and Nitriles

1.2.4. Generation and Alkylation of Dianions

1.2.5. Intramolecular Alkylation of Enolates

1.2.6. Control of Enantioselectivity in Alkylation Reac:ions

 1.3. The Nitrogen Analogs of Enols and Enolates: Enamines and Imine Anions

 General References

 Problems

Chapter 2. Reactions of Carbon Nucleophiles with Carbonyl Compounds

Introduction

 2.1. Aldol Addition and Condensation Reactions

2.1.1. The General Mechanism

2.1.2. Control of Regio- and Stereoselectivity of Aldol Reactions of Aldehydes and Ketones

2.1.3. Aldol Addition Reactions of Enolates of Esters and Other Carbonyl Derivatives

2.1.4. The Mukaiyama Aldol Reaction

2.1.5. Control of Facial Selectivity in Aldol and Mukaiyama Aldol Reactions

2.1.6. Intramolecular Aldol Reactions and the Robinson Annulation

 2.2. Addition Reactions of Imines and Iminium Ions

2.2.1. The Mannich Reaction

2.2.2. Additions to N-Acyl Iminium Ions

2.2.3. Amine-Catalyzed Condensation Reactions

 2.3. Acylation of Carbon Nucleophiles

2.3.1. Claisen and Dieckmann Condensation Reactions

2.3.2. Acylation of Enolates and Other Carbon Nucleophiles

 2.4. Olefination Reactions of Stabilized Carbon Nucleophiles

2.4.1. The Wittig and Related Reactions of Phosphorus-Stabilized Carbon Nucleophiles

2.4.2. Reactions of a-Trimethyisilylcarbanions with Carbonyl Compounds

2.4.3. The Julia Olefination Reaction

 2.5. Reactions Proceeding by Addition-Cyclization

2.5.1. Sulfur Yiides and Related Nucleophiles

2.5.2. Nucleophilic Addition-Cyclization of ot-Haloesters

 2.6. Conjugate Addition by Carbon Nucleophiles

2.6.1. Conjugate Addition of Enolates

2.6.2. Conjugate Addition with Tandem Alkylation

2.6.3. Conjugate Addition by Enolate Equivalents

2.6.4. Control of Facial Selectivity in Conjugate Addition Reactions

2.6.5. Conjugate Addition of Organometallic Reagents

2.6.6. Conjugate Addition of Cyanide Ion

 General References

 Problems

Chapter 3. Functional Group Interconversion by Substitution, Including Protection and Deprotection

Chapter 4. Electrophilic Additions to Carbon-Carbon Multiple Bonds

Chapter 5. Reduction of Carbon-Carbon Multiple Bonds, Carbonyl Croups, and Other Functional Groups

Chapter 6. Concerted Cycloadditions, Unimolecular Rearrangements, and Thermal Eliminations

Chapter 7. Organometallic Compounds of Group I and II Metals

Chapter 8. Reactions Involving Transition Metals

Chapter 9. Carbon-Carbon Bond-Forming Reactions of Compounds of Boron, Silcon, and Tin

Chapter 10. Reactions Involving Carbocations, Carbenes, and Radicals and Reactive Intermediates

Chapter 11. Aromatic Substitution Reactions

Chapter 12. Oxidations

Chapter 13. Multistep Syntheses

References

Index