Phase Transfer Catalysis

Preface

Chapter 1 Introduction

I. Phase Transfer Catalysis

II. History

III. Systems Related to Phase Transfer Catalysis

References

Chapter 2 Mechanism and Rates in Phase Transfer Catalyzed Reactions

I. General Considerations

II. Transfer of Anions from Aqueous to Organic Phases

III. Ionic Reactions in Nonpolar Media

IV. Mechanism Sequences and Kinetics of Phase Transfer Catalysis with Slow Organic Phase Reactions

V. Mechanism Sequences and Kinetics of Phase Transfer Catalysis with Fast Organic Phase Reactions

References

Chapter 3 Catalysts

I. General Comparison of Phase Transfer Catalysts

II. Quaternary Salts as Catalysts

III. Macrocyclic Ethers as Phase Transfer Catalysts

References

Chapter 4 Simple Displacement Reactions

I. General Considerations

II. Cyanide Displacement

III. Halide Displacement Reactions

IV. Hydroxide, Alkoxide, Phenoxide, and Thiophenoxide Displacement Reactions

V. Carboxylate Ion Displacements

VI. Displacement Reactions with Azide Ion

VII. Superoxide Anion

VIII. Other Anions

References

Chapter 5 Phase Transfer Catalyzed Alkylation and Condensation Reactions

I. General Considerations

II. Alkylation and Arylation of Activated Nitriles

III. Darzen's Reaction with Chloroacetonitrile

IV. Michael Reactions

V. Alkylation of Esters and Keto Esters

VI. Alkylation of Ketones

VII. Aldehyde Reactions

VIII. Alkylation of Cyclopentadienes

IX. Alkylation of Sulfones and Other Sulfur Compounds

X. N-Alkylations

References

Chapter 6 Generation and Reaction of Dihalocarbenes and Other Carbenes in Phase Transfer Catalyzed Systems

I. General Considerations

II. Addition of Dihalocarbenes to Olefins

III. Dihalocarbene Insertion Reactions into C—H Bonds

IV. Reaction of PTC-Generated Dihalocarbenes with Nitrogen Compounds

V. Reaction of Dichlorocarbene with Alcohols

VI. Reaction of Dichlorocarbene with Aldehydes

VII. Other Carbene Reactions Using Phase Transfer Catalysts

References

Chapter 7 Phase Transfer Catalysis of Ylide-Mediated Reactions

I. The Wittig Reaction with Aqueous Sodium Hydroxide

II. The Wittig-Horner Reaction

III. Sulfur Ylides

References

Chapter 8 Phase Transfer Catalyzed Oxidation and Reduction Reactions

I. Oxidation

II. Reductions

References

Chapter 9 Miscellaneous Phase Transfer Catalyzed Reaction Systems

I. Elimination Reactions

II. Hydrolysis Reactions

III. Deuterium Exchange of Active Hydrogens

IV. Aldehyde Condensations

V. Thiolation with Organic Thiocyanates

VI. Preparation of α-Diazo Compounds from Tosyl Azide and Active Methylene Compounds

VII. Phosphorylation Reactions

VIII. Reactions with Metal Carbonyls

References

Index