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.

PrefaceAcknowledgmentsContents of Volume IChapter I IntroductionChapter 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" ResultsChapter III Ozonation of Aromatic Compounds: Benzene and Substituted Benzenes I. General Overview A. Historical Background ¿. 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. AlkenylferrocenesChapter 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. SummationChapter 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 ConclusionsChapter 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 PyrimidinesChapter 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 ¿. 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. IodineChapter 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. MiscellaneousChapter 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. MiscellaneousChapter 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. MiscellaneousChapter 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: AntiozonantsChapter XII Ozonation of Olefins Revisited I. Introduction II. Ozone III. Mechanism of Liquid-Phase Ozonolysis of Olefins A. The Unstable Ozonolysis Intermediates ¿ . 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 OlefinsEpilogueOverview and Miscellaneous New DevelopmentsBibliographyIndex