
Ozonation in Organic Chemistry V1
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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
Acknowledgments
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
Epilogue
Overview and New Developments
Bibliography
Index
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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