Phase Transfer Catalysis

Phase Transfer Catalysis

Principles and Techniques

1st Edition - November 28, 1978

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  • Editor: Charles Liotta
  • eBook ISBN: 9780323153300

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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

  • Preface

    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



Product details

  • No. of pages: 378
  • Language: English
  • Copyright: © Academic Press 1978
  • Published: November 28, 1978
  • Imprint: Academic Press
  • eBook ISBN: 9780323153300

About the Editor

Charles Liotta

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