Ozonation in Organic Chemistry V2

Ozonation in Organic Chemistry V2

Nonolefinic Compounds

1st Edition - April 28, 1982

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  • Author: Philip S. Bailey
  • eBook ISBN: 9780323147439

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Ozonation in Organic Chemistry, Volume II: Nonolefinic Compounds discusses the reactions of ozone with organic compounds. The book presents the role of ozone in air pollution. It demonstrates the use of ozonation in wastewater purification, effects of ozone on biological systems, and degradation of rubber. The text describes the ozonation of acetylenic compounds, benzene, and substituted benzenes. It discusses the bond attack on benz-fused carbocyclics. Another topic of interest is the mechanism of ozonation of anthracene. The section that follows describes the electrophilic ozone attack on nitrogen. The book will provide valuable insights for chemists, environmentalists, students, and researchers in the field of organic chemistry.

Table of Contents

  • Preface


    Contents of Volume I

    Chapter I Introduction

    Chapter II Ozonation of Acetylenic Compounds

    I. Historical Overview

    A. Products

    B. Early Mechanistic Concepts

    II. Present-Day Mechanistic Concepts

    A. The Criegee Mechanism

    B. The Initial Ozone Attack, Adduct, and Subsequent Intermediates

    III. Vapor-Phase Ozonation of Acetylenes

    IV. Miscellaneous Synthetic Applications and Novel or "Anomalous" Results

    Chapter III Ozonation of Aromatic Compounds: Benzene and Substituted Benzenes

    I. General Overview

    A. Historical Background

    Β. Comparison with Other Systems

    C. Nonperoxidic Ozonolysis Products

    II. Mechanism of Ozonation of Benzenoid Compounds

    A. General Mechanistic Scheme

    B. Peroxidic Ozonolysis Products

    C. Initial Ozone Attack

    D. Summation and Conclusions

    III. Vapor-Phase Ozonations

    IV. Ozonation of Phenols

    V. Practical Applications

    VI. Alkenylferrocenes

    Chapter IV Ozonation of Aromatic Compounds: Bond Attack on Benz-Fused Carbocyclics

    I. Introduction

    II. Naphthalenes

    A. Historical General Overview

    B. Peroxidic Ozonolysis Products and Mechanism

    C. Nonperoxidic Ozonolysis Products. Utility of Ozonolysis of Naphthalenes

    III. Triphenylene and Perylene

    IV. Phenanthrenes

    A. General Overview

    B. Peroxidic Ozonolysis Products. Mechanism

    C. Nonperoxidic Ozonolysis Products. Utility

    D. 4,5-Methylenephenanthrene

    E. Miscellaneous

    V. Phenanthrene-Like Poly cyclic Aromatic Hydrocarbons

    A. Chrysene

    B. Benzo[c]phenanthrene

    C. Picene

    D. Benzo[g]chrysene

    E. Dibenzo[c,g]phenanthrene and Coronene

    F. Dibenzo[g,p]chrysene

    VI. Summation

    Chapter V Ozonation of Aromatic Compounds: Bond Attack versus Atom Attack on Benz-Fused Carbocyclics

    I. Pyrene-Type Benz-Fused Carbocyclics

    A Pyrene

    B. Benzo[a]pyrene

    C. Benzo[r,s,t]pentaphene

    D. Summation

    II. Anthracene and Substituted Anthracenes

    A. General Overview

    B. Mechanism of Ozonation of Anthracene

    C. 9,10-Dimethylanthracene and Related Compounds

    D. 9,10-Dihaloanthracenes

    E. Other Substituted Anthracenes—A Summary

    III. Benz[a]anthracene and Derivatives

    A. General Overview

    B. Mechanism of Ozonation of Benz[a]anthracene

    C. 7,12-Dimethylbenz[a]anthracene

    D. 3-Methylcholanthrene

    IV. Other Anthracene-Type Benz-Fused Aromatics

    A. Naphthacene

    B. Dibenz[a,h]anthracene

    C. Dibenz[a,j]anthracene

    D. Pentaphene

    V. Summation and Conclusions

    Chapter VI Ozonation of Aromatic Compounds: Heterocyclics

    I. Introduction

    II. Furans

    A. Alkylfurans

    B. Arylfurans and Mechanism of Ozonation of Furans

    C. Practical Aspects

    III. Pyrroles

    A. General

    B. Mechanism of Ozonation of Pyrroles

    IV. Thiophenes

    V. Other Five-Membered Ring Heterocycles

    A. Pyrazoles

    B. Isoxazoles

    C. Furoxans and Osotriazole Oxides

    D. Arsenic Heterocycle

    VI. Indoles and Other Benz-Fused Five-Membered Ring Heterocycles

    A. Introduction

    B. Mechanism of Ozonation of Indoles

    C. Miscellaneous Applications of Ozonation of Indoles

    D. Benzofurans, Benzothiophenes, and Similar Heterocycles

    VII. Pyridine and Other Six-Membered Ring Heterocycles

    A. Pyridine and Homologs

    B. 4-Pyrones

    VIII. Quinoline and Other Benz-Fused Six-Membered Ring Heterocycles

    A. Quinolines

    B. Isoquinolines

    C. Benzoquinoline Types

    D. Benzopyrylium Salts

    IX. Purines and Pyrimidines

    Chapter VII Ozonation of Nucleophiles

    I. Introduction

    II. Electrophilic Ozone Attack on Nitrogen

    A. Historical Background

    B. Reactivity of Amines with Ozone

    C. Amine Oxide Formation versus Side-Chain Oxidation: Tertiary Amines

    D. Ammonia

    E. Primary Amines

    F. Secondary Amines

    G. Hydroxylamines and Nitrosoalkanes

    H. Miscellaneous

    I. Summation of Reactions of Amines with Ozone

    III. Electrophilic Ozone Attack on Other Elements of Group V: Phosphites

    IV. Electrophilic Ozone Attack on Sulfur

    A. Thioethers: Liquid Phase

    Β. Di and Tetrasulfides: Liquid Phase

    C. Miscellaneous Sulfur Compounds: Liquid Phase

    D. Vapor-Phase Ozonations

    E. Miscellaneous Applications

    V. Electrophilic Ozone Attack on Other Elements of Groups VI and VII

    A. Selenium

    B. Oxygen

    C. Iodine

    Chapter VIII Ozonation of Hetero Multiple Bonds

    I. Carbon-Nitrogen Double Bonds

    A. Introduction and Survey

    B. Mechanisms of Ozonation of Carbon-Nitrogen Double Bonds

    C. Special Examples

    II. Carbon-Sulfur Double Bonds

    III. Carbon-Oxygen Double Bonds

    IV. Miscellaneous

    Chapter IX Ozone Attack at sp3 Carbon Centers: Ozonation of Carbon-Hydrogen Bonds

    I. Introduction

    II. General Survey

    A. Alkanes

    B. Cycloalkanes

    C. Alkyl-Substituted Aromatics

    D. Other Unactivated Methylene and Methyne Groups

    III. The Mechanistic Spectrum

    IV. Unactivated Carbon-Hydrogen Bonds

    A. Mechanism of Liquid-Phase Ozonation

    B. Further Rationalizations

    C. Vapor-Phase Ozonation

    D. Alkyl-Substituted Aromatics

    E. Ozonation of Unactivated Carbon-Hydrogen Bonds: A Summary

    V. Activated Carbon-Hydrogen Bonds

    A. Ozonation of Alcohols: General Overview

    B. Ozonation of Ethers: General Overview

    C. Mechanism of Ozonation of Alcohols and Ethers

    D. Ozonation of Acetals and Glycosides

    E. Ozonation of Aldehydes

    VI. Deactivated Carbon-Hydrogen Bonds

    A. Ozonation of Ketones

    B. Ozonation of Carboxylic Acids

    C. Miscellaneous

    VII. Ozonation of Polymers and Miscellaneous Substrates

    A. Polymers

    B. Miscellaneous

    VIII. Special Techniques and Applications

    A. Dry Ozonation

    B. Ozonations in "Superacid" Solutions

    C. Miscellaneous

    Chapter X Ozonation of Miscellaneous Organic Species

    I. Introduction

    II. Ozonation of Organic Heteroatom Compounds of Group IVA: Organometallics

    A. Organosilicon Compounds

    B. Other Organic Heteroatom Compounds of Group IVA

    C. Other Organometallic Compounds

    III. Ozonolysis of the Cyclopropane Ring

    IV. Cleavage of sp3 Carbon-Carbon Bonds by Ozone

    V. Ozone as a Nucleophile: Ozonation of Carbocations

    VI. Radical Reactions of Ozone

    A. Introduction

    B. Hydroperoxides

    C. Aromatic Substitutions and Oxidations

    D. Ozonation in Aqueous Solution: Hydroxyl Radicals

    E. Freons

    F. Miscellaneous

    Chapter XI The Practical Side

    I. Introduction

    II. Techniques

    III. Synthesis

    IV. Analysis and Proof of Structure

    V. Water, Wastewater, and Sewage Purification

    VI. Pulping and Bleaching of Wood

    VII. Miscellaneous Uses

    VIII. The Ozone Layer Controversy

    IX. The Negative Side of Ozone Organic Chemistry

    A. Ozone in Air Pollution

    B. Effects of Ozone on Biological Systems: Toxicity

    C. Degradation of Rubber: Antiozonants

    Chapter XII Ozonation of Olefins Revisited

    I. Introduction

    II. Ozone

    III. Mechanism of Liquid-Phase Ozonolysis of Olefins

    A. The Unstable Ozonolysis Intermediates

    Β . 1,2,4-Trioxolane (Final Ozonide) Conformations

    C. The Mechanistic Steps

    D. Other Studies Concerning Routes to Peroxidic Ozonolysis Products

    E. Peroxidic Ozonolysis Products

    IV. Special and Unusual Ozonolyses and Ozonations

    A. Haloolefins

    B. Ozonation of Allenes

    C. Ozonation of Ketenes

    D. Ozonation of Vinylsilanes and Sulfides

    E. Epoxidation versus Ozonolysis

    F. "Anomalous" Ozonolyses

    V. Vapor-Phase Ozonation

    A. Mechanisms with Simple Olefins

    B. Haloolefins

    VI. Summary: Ozonation of Olefins


    Overview and Miscellaneous New Developments



Product details

  • No. of pages: 516
  • Language: English
  • Copyright: © Academic Press 1982
  • Published: April 28, 1982
  • Imprint: Academic Press
  • eBook ISBN: 9780323147439

About the Author

Philip S. Bailey

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