Phase Transfer Catalysis - 1st Edition - ISBN: 9780126636604, 9780323153300

Phase Transfer Catalysis

1st Edition

Principles and Techniques

Editors: Charles Liotta
eBook ISBN: 9780323153300
Imprint: Academic Press
Published Date: 28th November 1978
Page Count: 378
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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.

Table of Contents


Chapter 1 Introduction

I. Phase Transfer Catalysis

II. History

III. Systems Related to Phase Transfer Catalysis


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


Chapter 3 Catalysts

I. General Comparison of Phase Transfer Catalysts

II. Quaternary Salts as Catalysts

III. Macrocyclic Ethers as Phase Transfer Catalysts


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


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


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


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


Chapter 8 Phase Transfer Catalyzed Oxidation and Reduction Reactions

I. Oxidation

II. Reductions


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




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© Academic Press 1978
Academic Press
eBook ISBN:

About the Editor

Charles Liotta

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