Catalytic Hydrogenation in Organic Syntheses

PrefaceChapter 1 Hydrogenation Catalysts, Reactors, and Reaction Conditions I. General Considerations II. Reaction Conditions and Catalyst Variables III. Hydrogenation Reactors IV. Preparation of Catalysts ReferencesChapter 2 Hydrogenation of Acetylenes I. General Considerations II. Catalysts III. Acetylenic Carbinols and Glycols IV. Hydrogenolysis V. Acetylenic Aldehydes and Ketones VI. Polyacetylenes ReferencesChapter 3 Hydrogenation of Olefins I. Mechanism of Hydrogenation II. Catalysts III. Effect of Olefin Structure IV. Double-Bond Migration V. Effects of Double-Bond Migration VI. Cis-Trans Isomerization VII. Stereochemistry VIII. Vinyl Functions IX. Unsaturated Carbonyl Compounds ReferencesChapter 4 Hydrogenation of Acids, Esters, Lactones, and Anhydrides I. Hydrogenation of Acids II. Hydrogenolysis of Esters III. Hydrogenation of Lactones IV. Hydrogenation of Anhydrides ReferencesChapter 5 Hydrogenation of Aldehydes I. Saturated Aliphatic Aldehydes II. Unsaturated Aliphatic Aldehydes III. Aromatic Aldehydes IV. Aromatic Unsaturated Aldehydes ReferencesChapter 6 Hydrogenation of Ketones I. Aliphatic Ketones II. Aromatic Ketones ReferencesChapter 7 Hydrogenation of Nitro Compounds I. Catalysts II. Solvents III. Partial Reduction of Nitro Compounds IV. Reduction of Aliphatic Nitro Compounds V. Unsaturated Nitro Compounds VI. Halonitro Aromatics VII. Dinitro Compounds VIII. Cyclizations ReferencesChapter 8 Hydrogenation of Nitriles I. Mechanism II. Catalysts III. Unsymmetrical Amines IV. Cyclizations V. Reductive Hydrolysis VI. Methylation ReferencesChapter 9 Hydrogenation of Oximes I. Catalysts II. Substrates III. Solvent IV. Products of Partial Reduction V. Products of Hydrolysis VI. Bifunctional Molecules VII. Stereochemistry ReferencesChapter 10 Reductive Alkylation I. Substrates II. Catalysts III. Stereochemistry ReferencesChapter 11 Hydrogenation of Carbocyclic Aromatics I. Carbocyclic Aromatics II. Anilines III. Phenols and Phenyl Ethers ReferencesChapter 12 Hydrogenation of Heterocyclic Compounds I. Pyridines II. Pyrroles III. Indoles IV. Quinolines and Isoquinolines V. Imidazoles and Imidazolones VI. Pyrazines VII. Pyrimidines VIII. Furans ReferencesChapter 13 Catalytic Dehydrohalogenation I. Catalysts II. Basic Media III. Effect of Structure IV. Elimination Reactions V. Halohydrins VI. Haloolefins VII. Halonitro Compounds VIII. Polyhalo Compounds IX. Halogen as Blocking Group X. Trapping Reactions ReferencesChapter 14 Hydrogenolysis of Small Rings I. Cyclopropanes II. Oxiranes III. Aziridines ReferencesChapter 15 Miscellaneous Hydrogenolyses I. Benzyl Groups Attached to Oxygen II. Benzyl Groups Attached to Nitrogen III. Allylic Oxygen Compounds IV. Hydrogenolysis of the Carbon-Carbon Bond V. Hydrogenolysis of the Oxygen-Oxygen Bond VI. Hydrogenolysis of the Nitrogen-Oxygen Bond VII. Hydrogenolysis of the Nitrogen-Nitrogen Bond ReferencesIndex