Organic Syntheses by Oxidation with Metal Compounds

This book is concerned with the synthetic aspects of oxidation reactions involving metal compounds. which are readily available or easy to prepare. The sequence followed in the chapters is as follows: a general introduction. a limited treatment of reaction mechanisms to serve as a basis for synthesis. and scope and limitations of the oxidant system. mostly in terms of substrate and product classes. Finally, at the end of each chapter. representative synthetic procedures are given together with relevant experimental considerations. A general table is included as an appendix. This contains substrate classes and resulting product classes, referring to the oxidative procedures in the chapters. The table provides the synthetic organic chemist with a quick overview of oxidation possibilities with metal-contain­ ing oxidants, enabling him to select the right method for his purpose. The editors hope that not only organic research chemists in industry and at universities, but also advanced undergraduate and graduate students in organic chemistry, will find this book a useful guide in the design, understanding, and practical performance of oxidative organic syntheses. The editors are grateful to the authors not only for their contributions. containing interesting new developments in oxidation chemistry, but also for the way they fitted the text into the general framework given for the book. Their suggestions and comments are gratefully acknowledged. Thanks are also due to Mrs. A. I. Rohnstrom-Ouwejan, secretary to the editors, for her administrative support.

Inhalt
1. Oxidation by Vanadium Compounds.- 1. Introduction.- 2. Mechanisms.- 2.1 Alkanes, Alkylaromatics, and Aromatic Compounds.- 2.2 Carbon-Carbon Double Bonds: Synthesis of Epoxides and Glycols.- 2.3 Hydroxy Compounds.- 2.3.1 Alcohols.- 2.3.2 Phenols and Hydroquinones.- 2.4 Carbonyl Compounds: Ketones and Quinones.- 2.5 Nitrogen Compounds.- 2.6 Sulfur Compounds.- 2.6.1 Oxidation of Thiols.- 2.6.2 Oxidation of Sulfides and Sulfoxides.- 3.Scope and Limitations.- 3.1 Oxidation of Alkanes.- 3.2 Oxidation and Ammoxidation of Aikylaromatics.- 3.3 Oxidation of Aromatic Compounds.- 3.4 Oxidation of Carbon-Carbon Double Bonds.- 3.5 Oxidation of Alcohols.- 3.5.1 Primary Alcohols.- 3.5.2 x-Acetylenic Alcohols.- 3.5.3 Cyclobutanols.- 3.5.4 Phenols and Phenyl Ethers.- 3.6 Carbonyl Compounds.- 3.7 Nitrogen Compounds.- 3.8 Sulfur Compounds.- 3.8.1 Thiols.- 3.8.2 Sulfides and Sulfoxides.- 3.8.3 Disulfides.- 4.Experimental Considerations and Procedures.- 4.1 General Considerations.- 4.2 General Procedures and Typical Detailed Procedures.- 4.2.1 Epoxidation of Carbon-Carbon Double Bonds.- 4.2.2 Oxidation of Alcohols.- 4.2.3 Intramolecular Oxidative Coupling of Phenols.- 4.2.4 Oxidation of Nitrogen Compounds.- 4.2.5 Oxidation of Sulfur Compounds.- 4.2.5a. Synthesis of ?-Hydroxysulfoxides.- 4.2.5b. Oxidation of Sulfides.- References.- 2. Oxidation by Oxochromium(VI) Compounds.- 1. Introduction.- 2. Mechanisms.- 2.1.Carbon-Hydrogen Bonds.- 2.1.1 Alkanes and Cycloalkanes.- 2.1.2 Allylic Oxidations.- 2.1.3 Benzylic Oxidations.- 2.2 Carbon-Carbon Double Bonds.- 2.3 Hydroxy Compounds.- 2.3.1 Alcohols.- 2.3.2 Diols.- 2.4 Ethers.- 2.5 Carbonyl Compounds.- 2.5.1 Aldehydes.- 2.5.2 Ketones.- 2.6 Carboxylic Acids.- 2.7 Nitrogen Compounds.- 2.8 Sulfur Compounds.- 2.9 Organic Halides.- 3.Scope and Limitations.- 3.1 Oxidation of Alkanes and Cycloalkanes.- 3.2 Oxidation of Allylic Carbon-Hydrogen Bonds.- 3.3 Oxidation of Carbon-Hydrogen Bonds Adjacent to Triple Bonds.- 3.4 Oxidation of Alkylbenzenes.- 3.5 Oxidation of Hydrindacenes, Indans, Tetralins, and Acenaphthenes.- 3.6 Oxidation of Aromatic Rings.- 3.7 Oxidation of Unsaturated Systems.- 3.7.1 Nonfunctionalized Alkenes and Polyenes.- 3.7.2 Functionalized Alkenes.- 3.7.3 Alkynes.- 3.8.Oxidation of Hydroxy Compounds.- 3.8.1 Alcohols.- 3.8.2 Carbohydrates.- 3.8.3 Phenols.- 3.9 Oxidation of Ethers.- 3.10 Oxidation of Silyl Ethers.- 3.11 Oxidation of Carbonyl Compounds.- 3.11.1 Aldehydes.- 3.11.2 Ketones.- 3.12.Oxidation of Carboxylic Acids and Their Derivatives.- 3.12.1 Carboxylic Acids.- 3.12.2 Esters.- 3.13.Oxidation of Nitrogen Compounds.- 3.13.1 Amines.- 3.13.2 Amides.- 3.13.3 Oximes.- 3.13.4 Imines.- 3.14 Oxidation of Sulfur Compounds.- 3.15 Oxidation of Organic Halides.- 3.16 Oxidation of Organoboranes.- 4.Experimental Considerations and Procedures.- 4.1. General Considerations.- 4.2. General Procedures and Typical Detailed Procedures.- 4.2.1 Carbon-Hydrogen Bonds.- 4.2.2 Allylic Carbon-Hydrogen Bonds.- 4.2.3 Alkylaromatics.- 4.2.4 Indans and Tetralins.- 4.2.5 Alkenes.- 4.2.6 Alcohols.- 4.2.7 Benzyl Ethers.- 4.2.8 Silyl Ethers.- 4.2.9 Trialkyloxyboroxines.- 4.2.10 Esters.- 4.2.11 Oximes.- 4.2.12 Organoboranes.- References.- 3. The Oxidation of Organic Compounds by Active Manganese Dioxide.- 1.Introduction.- 1.1.Types and Methods of Preparation of Active Manganese Dioxide.- 1.1.1 Standardization of Active Manganese Dioxide.- 1.1.2 Preparation of Very Active Manganese Dioxide.- 1.1.3 Preparation of Active Manganese Dioxide.- 1.1.4 Preparation of Active y-Manganese Dioxide.- 1.2 Effects of Solvent on Oxidation.- 1.3 Time and Temperature Effects on Oxidation.- 1.4 Structure of Active Manganese Dioxide.- 2.Mechanism.- 2.1 Free-Radical Mechanism.- 2.2 Ionic Mechanism.- 2.2.1 Cyclic Transition Intermediate.- 2.2.2 Manganic Ester Intermediate.- 3.Oxidation of Alcohols and Hydroxy Compounds.- 3.1.?,?-Unsaturated Alcohols (?,?-Ethylenic Primary and Secondary Alcohols).- 3.1.1 Vitamin A, and Analogs.- 3.1.2 ?,? -Ethylenic, Primary and Secondary Alcohols.- 3.1.3 Oxidation of cis- and fra/w-Unsaturated Alcohols.- 3.1.4 ?,?-Unsaturated Lactones.- 3.1.5 Additional Pertinent Oxidations.- 3.1.6 ?,? -Unsaturated Diols and Polyols.- 3.1.7 Conjugative Activation of ?-Hydroxyl Groups in Unsaturated Alcohols.- 3.1.8 Oxidation of ?,?-Unsaturated Aldehydes.- 3.2.Acetylenic Alcohols.- 3.2.1 ?,?-Unsaturated Acetylenic Alcohols.- 3.2.2 Oxidation of Alkynic Alcohols of Type R - CHOH - C = CH.- 3.2.3 Oxidation of Acetylenic Alcohols in the Presence of Amines.- 3.3.Terpenes.- 3.3.1 The Stereospecific Corey Esterification.- 3.3.2 Selective Oxidations of Terpenes.- 3.3.3 Synthesis of Sesquicarene.- 3.3.4 Rearrangement of Terpenes.- 3.4.Steroids.- 3.4.1 Oxidation of Unsaturated Steroid Alcohols in Ring A, B, C, or D.- 3.4.2 Steroidal Alkaloids.- 3.4.2a. Oxidation of an Active Methylene Group in Solacon-gestidine.- 3.4.2b. Active Manganese Dioxide: A Reagent for a Biomimetic Cyclization.- 3.5 Alkaloids.- 3.6 Benzyiic Alcohols.- 3.6.1 Oxidation of Phthalyl Alcohols.- 3.6.2 Oxidation of Benzenemethanols.- 3.6.3 Favored Oxidation of Benzyiic Hydroxyl Groups.- 3.6.4 Oxidation in the Vitamin D Series.- 3.6.5 Conversion of ?-Hydroxy Acids into Keto Acids.- 3.7 Heterocyclic Alcohols.- 3.8 Saturated Aliphatic Alcohols.- 3.9 Polyhydroxy Compounds.- 3.10 Carbohydrates.- 3.10.1 Synthesis of Alditols.- 3.10.2 Application of the Corey Procedure.- 3.10.3 Application of the Mannich Base.- 3.10.4 Other Applications.- 3.11.Phenols.- 3.11.1 Oxidative Coupling of Phenols.- 3.11.2 Oxidative Polymerization of Phenols.- 3.12.Benzilic Acid Type Rearrangements.- 3.12.1 Oxidative Ring Contraction of Carotenoid Diosphenols.- 3.12.2 Oxidative Ring Contraction of Steroids.- 4.Dehydrogenation and Oxidative Aromatization.- 4.1.Dehydrogenation.- 4.1.1 Dehydrogenation at Carbon or Carbon-Hetero Atom.- 4.1.2 Dehydrogenation in the Diazepine Series.- 4.2.Oxidative Aromatization.- 5.Hydrocarbons.- 5.1.Some Chemical Applications of Precipitated Manganese Dioxide in AcidMedia (e.g., Oxidation of Conjugated CH3-, CH2-, and =CH-Groups).- 5.1.1 Aromatic Systems.- 5.1.2 Other Systems.- 5.2.Oxidation of Conjugated CH3 -, CH: -, and =C-Groups by ManganeseDioxide in Neutral Media.- 5.2.1 Oxidation of Heteroaromatic Rings. Loss of Aromaticity.- 5.2.2 Oxidation of Alkyl Ferrocenes and Bridged Ferrocenes.- 6.Amines and Hydraz…

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