Ozonation in Organic Chemistry V1

Ozonation in Organic Chemistry V1

1st Edition - January 28, 1978

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  • Author: Philip S. Bailey
  • eBook ISBN: 9780323157483

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Ozonation in Organic chemistry, Volume I: Olefinic Compounds covers the historical background of ozone reactions with organic substances and the mechanisms of these reactions. Composed of 12 chapters, this book first deals with the development of the available theory of all ozone reactions, such as the Harries and Staudinger theories, particularly the Criegee mechanism of ozonolysis. This text then describes the step-by-step mechanism of the classical ozonolysis reaction of olefins and how it evolved. Considerable chapters are devoted to the reactions that compete with ozonolysis, such as epoxidation and other partial cleavage reactions. Both liquid- and gas-phase ozone reactions are explored in other chapters. This volume will appeal to those who are interested in exploring the frontiers of ozone-organic chemistry.

Table of Contents

  • Preface


    Tentative Contents of Volume II

    Chapter I Introduction

    I. Importance of Ozone Chemistry

    II. Historical

    A. Discovery: The Schönbein Period, 1840-1902

    B. Development: The Harries Period, 1903-1948

    C. Understanding and Utilization: The Criegee Period, 1949 to Present

    III. Scope and Terminology

    Chapter II The Ozone Molecule

    I. Resonance and Molecular Orbital Descriptions

    II. The Singlet Diradical Description

    III. Types of Ozone Attack

    Chapter III Ozonolysis of Olefins: Introduction

    I. Historical Perspective

    A. Contributions of Harries

    B. The Staudinger Mechanism

    C. The Criegee Mechanism

    II. Chronological Mechanistic Description

    Chapter IV Ozonolysis of Olefins: Initial Ozone Attack and Adduct

    I. The Primary Ozonide

    II. 1,3-Dipolar Cycloaddition

    A. Electrophilic Nature of Ozone in 1,3-Dipolar Cycloaddition

    B. Other Evidence for 1,3-Dipolar Cycloaddition

    Chapter V Ozonolysis of Olefins: The Peroxidic Products

    I. Ozonides

    A. Formation: Properties

    B. Spectral Properties: Identification

    II. Ketone and Aldehyde Diperoxides

    III. Polymeric Ozonides and Peroxides. Oligomers

    IV. α-Oxyalkyl Hydroperoxides

    Chapter VI Ozonolysis of Olefins: Routes to Peroxidic Products

    I. Evidence for Criegee Mechanism

    II. Stereochemistry. Flaws in Simple Criegee Mechanism

    III. The SMY Mechanism

    IV. Refinements of Criegee Mechanism

    A. Bauld-Bailey Scheme. SYN and Anti Carbonyl Oxides

    B. Kuczkowski Scheme

    C. Symmetrical and Unsymmetrical Olefins with Small Substituents at Double Bond

    D. Further Comparisons

    V. The "Unified Concept"

    VI. Weighing the Evidence: Criegee Carbonyl Oxide Confirmed

    A. 18O Studies

    B. Criegee's Last Contribution

    Chapter VII Ozonolysis of Olefins: Competitions in Peroxidic Product Formation

    I. Competitions in Nonparticipating Solvents

    A. Ozonide vs. Diperoxide and Oligomer Formation

    B. Effects of Various Experimental Conditions on Ozonide Formation

    C. Peroxy Epoxides

    D. Summation

    II. Competitions in Participating Solvents

    A. α-Oxyalkyl Hydroperoxide Formation

    B. Amozonolysis, Cyanozonolysis

    C. Ozonide Formation in Participating Solvents

    D. Intramolecular Interactions

    III. Direction of Cleavage of Primary Ozonides of Unsymmetrical Olefins

    IV. Summary of Routes to Peroxidic Products

    Chapter VIII Ozonolysis of Olefins: Routes from Peroxidic to Nonperoxidic Products

    I. Reductive. Nucleophilic Displacement at Oxygen

    II. Other Reductive Methods

    A. Borane

    B. Glyoxalic Acid

    C. Tetracyanoethylene

    D. Catalytic

    III. Acid-Catalyzed Decompositions. Solvolysis

    A. "Acidolysis"

    B. Hydrolysis of α-Oxyalkyl Hydroperoxides

    IV. Base-Catalyzed Decompositions

    V. Pyrolysis and Photolysis

    VI. Miscellaneous

    Chapter IX "Anomalous" Ozonolysis of Olefins

    I. Introduction and General Theory

    II. Allylic Compounds

    III. α,β-Unsaturated Carbonyl Compounds

    IV. 1,4-Naphthoquinones

    V. Cinnamic Esters

    VI. Miscellaneous Types

    A. Camphene and Other Cyclic Systems

    B. Simple Olefins

    C. Miscellaneous

    D. Feist's Acid

    VII. Thermal and Photochemical

    Chapter X "Special" Liquid-Phase Ozonolyses

    I. Haloethylenes

    II. Unsaturated Oxyphosphoranes

    III. Alienes

    IV. Miscellaneous

    A. Cycloheptatrienes and Cyclooctatetraene

    B. Benzvalene

    Chapter XI Electrophilic Ozone Attack on Olefins. Epoxides and Other "Partial Cleavage" Products

    I. Introduction

    II. Examples

    III. Theory of Competition between Ozonolysis and "Partial Cleavage"

    A. Hindered Olefins

    B. Unhindered Olefins

    IV. Low-Temperature Studies, π Complexes

    V. Highly Hindered Olefins. Radical Formation with Vinyl Alcohols

    Chapter XII Gas-Phase Ozonation of Olefins

    I. Kinetics

    II. Products

    III. Mechanisms

    A. The Initial Ozone Attack. The Criegee Mechanism

    B. The O'Neal-Blumstein Mechanism

    IV. Special Types

    A. 1,3-Butadiene and Aliene

    B. Haloethylenes

    V. Solid-Gas Phase Ozonolyses


    Overview and New Developments



Product details

  • No. of pages: 288
  • Language: English
  • Copyright: © Academic Press 1978
  • Published: January 28, 1978
  • Imprint: Academic Press
  • eBook ISBN: 9780323157483

About the Author

Philip S. Bailey

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