Phase Transfer Catalysis

Phase Transfer Catalysis: Principles and Techniques outlines the theory, mechanism, and kinetics of the phase transfer catalysis (PTC) process.

This book surveys the principal reaction types that have employed the PTC, including the typical experimental procedures for preparing catalysts and conducting representative types of chemical reactions. This compilation discusses the transfer of anions from aqueous to organic phases, macrocyclic ethers as phase transfer catalysts, halide displacement reactions, and Darzen's reaction with chloroacetonitrile. The dihalocarbene insertion reactions into C-H bonds, Wittig reaction with aqueous sodium hydroxide, and phase transfer catalyzed oxidation and reduction reactions are also elaborated. This text likewise covers the deuterium exchange of active hydrogens and thiolation with organic thiocyanates.

This publication is beneficial to chemists and students studying the principles and techniques related to PTC.

Inhalt
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 a-Diazo Compounds from Tosyl Azide and Active Methylene Compounds


VII. Phosphorylation Reactions


VIII. Reactions with Metal Carbonyls


References


Index

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