Metal-Catalyzed Oxidations of Organic Compounds

Mechanistic Principles and Synthetic Methodology Including Biochemical Processes

1st Edition - October 28, 1981
Author: Roger Sheldon
Language: English
eBook ISBN:
9 7 8 - 0 - 3 2 3 - 1 5 0 0 4 - 0

Metal-Catalyzed Oxidations of Organic Compounds: Mechanistic Principles and Synthetic focuses on the oxidative transformations of functional groups. This book explores oxidation as… Read more

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Metal-Catalyzed Oxidations of Organic Compounds: Mechanistic Principles and Synthetic focuses on the oxidative transformations of functional groups. This book explores oxidation as being extensively used in the laboratory synthesis of fine organic chemicals and in the manufacture of large-volume petrochemicals. Organized into two parts encompassing 13 chapters, this book starts with an overview of the mechanistic principles of oxidation–reduction in biochemical, organic, and inorganic systems. This text then proceeds with a discussion of the use of molecular oxygen, hydrogen peroxide, and alkyl hydroperoxides as primary oxidants. Other chapters explore stoichiometric oxidations with metal oxidants, which include permanganate and chromic acid. This book discusses as well the synthetic applications of catalytic oxidations as well as the technology of petrochemical oxidation. The final chapter deals with the autoxidations of sulfur, phosphorus, and nitrogen compounds. This book is intended for chemists involved in organic synthesis, catalysis, and organometallic chemistry, both in academic institutions and in industrial laboratories.

PrefaceGlossaryAbbreviationsChapter 1 Introduction to Metal-Catalyzed Oxidations I. Historical Development II. Sources of Hydrocarbons III. Definition of Oxidation IV. Mechanistic Principles of Metal-Catalyzed Oxidation V. Homogeneous and Heterogeneous Catalysis VI. Biochemical Oxidations VII. Synthetic Methodology for Organic Oxidations References Additional Reading Part One Mechanistic Principles of Metal-Catalyzed Oxidations Chapter 2 Oxidations with Molecular Oxygen I. Fundamentals of Radical-Chain Processes II. Aldehyde Autoxidation III. Olefin Autoxidation IV. Cooxidations V. Gas-Phase versus Liquid-Phase Processes VI. Inhibition of Autoxidations VII. Solvent Effects References Additional Reading Chapter 3 Metal Catalysis in Peroxide Reactions I. Homolytic Catalysis II. Heterolytic Catalysis References Additional Reading Chapter 4 Activation of Molecular Oxygen by Metal Complexes I. Oxygen Fixation: Historical Development II. Peroxometal Complexes: Structural Types III. Nucleophilic Peroxometal Complexes IV. Electrophilic Peroxometal Complexes V. Superoxo- and ì-Peroxometal Complexes VI. Oxygen Transfer from Coordinated Ligands References Additional Reading Chapter 5 Direct Homolytic Oxidation by Metal Complexes I. Aromatic Compounds II. Alkenes III. Alkanes IV. Carbonyl Compounds V. Alcohols and Glycols VI. Electrochemical Generation of Metal Oxidants References Additional Reading Chapter 6 Direct Oxidation by Oxometal (M=0) Reagents I. Oxometal Reagents: Mechanistic Formulations II. Allylic Oxidations III. Oxidation at the Carbon-Carbon Double Bond IV. Allylic Oxidation versus Double Bond Attack V. Oxoiron Species in Enzymatic Hydroxylation and Epoxidation VI. Oxidations of Alcohols VII. Phase-Transfer Catalysis in Oxidations with Oxometal Reagents References Additional Reading Chapter 7 Activation by Coordination to Transition Metal Complexes I. Palladium-Catalyzed Oxidations of Olefins in Aqueous Media II. Palladium-Catalyzed Oxidations of Olefins in Nonaqueous Media III. Oxidative Carbonylation of Olefins IV. Oxidation of Aromatic Compounds by Palladium(II) Complexes V. Oxidation of Alcohols to Carbonyl Compounds VI. Palladium(II)-Catalyzed Oxidations with Hydroperoxides VII. Activation of Alkanes by Metal Complexes References Additional Reading Chapter 8 Biochemical Oxidations I. Terminology II. Coenzymes and Prosthetic Groups III. Types of Oxidative Transformation IV. Mechanisms of Enzymatic Oxidation V. Biomimetic Oxygénations VI. Immobilized Enzymes References Additional Reading Part Two Synthetic Methodology for Metal-Catalyzed Oxidations Chapter 9 Olefins I. Autoxidation II. Epoxidation III. Allylic Oxidation IV. Glycol (Ester) Formation V. Oxidative Cleavage VI. Oxidative Ketonization VII. Oxidative Nucleophilic Substitution VIII. Oxidative Carbonylation IX. Oxidative Dimerization X. Conjugated Dienes XI. Acetylenes References Chapter 10 Aromatic Hydrocarbons I. Autoxidation II. Metal-Catalyzed Autoxidations of Alkylbenzenes to Carboxylic Acids III. Metal-Catalyzed Autoxidations of Alkylbenzenes to Aldehydes and Ketones IV. Metal-Catalyzed Oxidations of Alkylbenzenes to Benzylic Acetates V. Oxidative Nuclear Substitution VI. Oxidative Dimerization VII. Oxidative Cleavage References Chapter 11 Alkanes I. Formation of Alkyl Hydroperoxide II. Alcohol and Ketone from Alkane III. Carboxylic Acid Formation References Chapter 12 Oxygen-Containing Compounds I. Alcohols II. Ethers III. Glycols IV. Aldehydes V. Ketones VI. Phenols References Chapter 13 Nitrogen, Sulfur, and Phosphorus Compounds I. Nitrogen Compounds II. Sulfur Compounds III. Phosphorus Compounds References Additional Reading Index