Ozonation in Organic Chemistry V1

PrefaceAcknowledgmentsTentative Contents of Volume IIChapter 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 TerminologyChapter II The Ozone Molecule I. Resonance and Molecular Orbital Descriptions II. The Singlet Diradical Description III. Types of Ozone AttackChapter III Ozonolysis of Olefins: Introduction I. Historical Perspective A. Contributions of Harries B. The Staudinger Mechanism C. The Criegee Mechanism II. Chronological Mechanistic DescriptionChapter 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 CycloadditionChapter 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 HydroperoxidesChapter 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 ContributionChapter 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 ProductsChapter 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. MiscellaneousChapter 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 PhotochemicalChapter X "Special" Liquid-Phase Ozonolyses I. Haloethylenes II. Unsaturated Oxyphosphoranes III. Alienes IV. Miscellaneous A. Cycloheptatrienes and Cyclooctatetraene B. BenzvaleneChapter 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 AlcoholsChapter 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 OzonolysesEpilogueOverview and New DevelopmentsBibliographyIndex