Ozonation in Organic Chemistry V2
Nonolefinic Compounds
- 1st Edition - December 3, 2012
- Author: Philip S. Bailey
- Language: English
- Paperback ISBN:9 7 8 - 0 - 1 2 - 4 1 4 4 2 5 - 5
- eBook ISBN:9 7 8 - 0 - 3 2 3 - 1 4 7 4 3 - 9
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… Read more
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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.
Preface
Acknowledgments
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
Epilogue
Overview and Miscellaneous New Developments
Bibliography
Index
- Edition: 1
- Published: December 3, 2012
- Language: English
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