Catalytic Hydrogenation over Platinum Metals

PrefacePart I Catalysts, Equipment, and Conditions 1 Platinum Metal Catalysts I. Platinum Metals II. Types of Catalyst III. Synergism IV. Catalyst Stability V. Safety VI. Catalyst Reuse VII. Induction Periods VIII. Reproducibility of Catalysts IX. Inhibitors and Poisons X. Promoters XI. Preparation of Catalysts References 2 Hydrogenation Reactors I. Atmospheric Pressure Reactors II. Low Pressure Reactors III. Microreactors IV. High Pressure Reactors References 3 Reaction Conditions I. Temperature II. Amount of Catalyst III. Pressure IV. Agitation V. Mode of Addition VI. Solvents ReferencesPart II Hydrogenation of Carbon-Carbon Unsaturation 4 Acetylenes I. Catalytic Metal II. Modified Catalyst Systems III. Stereochemistry IV. Diacetylenes V. Vinylacetylenes VI. Hydrogenolysis References 5 Olefins I. Catalysts II. Effect of Solvent III. Effect of Olefin Structure IV. Double-Bond Migration V. Stereochemistry VI. Olefin Saturation in Polyfunctional Molecules ReferencesPart III Hydrogenation of Nitrogen Compounds 6 Imines I. Acidic Media II. Neutral or Basic Media III. Effect of Structure References 7 Azines I. Solvents II. Preparation of Azo Compounds References 8 Hydrazones I. Hydrogenolysis II. Disproportionation III. Hydrazines by Reductive Alkylation References 9 Oximes I. Catalysts II. Substrate III. Solvent IV. Products of Partial Reduction V. Oximino Ketones VI. Products of Interaction with Other Functions VII. Stereochemistry References 10 Nitroso Compounds I. Hydroxylamine II. N-Nitrosoamines III. C-Nitroso Compounds References 11 Nitro Compounds I. Catalysts II. Solvents III. Reduction of the Aromatic Nitro Group to the Amine IV. Reduction of Aliphatic Nitro Groups to the Amine V. Difunctional Compounds VI. Rearrangements VII. Loss of Nitrogen by Hydrogenolysis VIII. Products of Partial Reduction References 12 Nitriles I. Coupling Reactions: Secondary and Tertiary Amines II. Products of Reductive Hydrolysis III. Nitriles with Other Functional Groups ReferencesPart IV Carbonyl Compounds 13 Hydrogenation of Acids, Esters, and Anhydrides I. Acids II. Esters III. Anhydrides References 14 Hydrogenation of Aldehydes I. Saturated Aliphatic Aldehydes II. Aromatic Aldehydes III. Unsaturated Aldehydes References 15 Hydrogenation of Ketones I. Aliphatic Ketones II. Aromatic Ketones III. Stereochemistry References 16 Reductive Alkylation-Preparation of Amines I. Substrates II. Catalysts III. Stereochemistry IV. Incipient Amine and Carbonyl Compounds References 17 Reductive Alkylation-Alkylidene Derivatives Text ReferencesPart V Hydrogenation of Aromatics 18 Carbocyclic Aromatics I. Comparison of Catalysts II. Partial Reduction of Aromatic Rings III. Strained Rings IV. Selective Hydrogenation V. Reduction of Benzyl Compounds VI. Fused Rings VII. Stereochemistry References 19 Phenols and Phenyl Ethers I. Platinum Metals II. Effect of Catalyst and Temperature on Stereochemistry III. Hydrogenolysis without Ring Reduction IV. Partial Ring Reduction V. Ring Saturation without Hydrogenolysis VI. Ring Reduction with Hydrogenolysis References 20 Anilines I. Reduction to the Saturated Amine II. Secondary Amines III. Hydrogenolysis IV. Hydrolysis References 21 Furans I. Hydrogenation of the Furan Nucleus II. Hydrogenolysis of Furans References 22 Nitrogen Heterocyclic Compounds I. Pyrroles II. Indoles III. Pyridines IV. Quinolines and Isoquinolines V. Imidazoles VI. Pyridazines VII. Pyrazines VIII. Pyrimidines ReferencesPart VI Hydrogenolysis 23 Hydrogenation of Acid Chlorides—Rosenmund Reduction I. Catalyst Regulators II. Side-Reactions III. Procedure IV. Selective Hydrogenation References 24 Catalytic Dehalogenation I. Catalysts II. Dehalogenation in Basic Media III. Choice of Base IV. Halogen Compounds with Other Functions V. Selective Hydrogenation of Polyhalo Compounds VI. Rearrangements VII. Coupling Reactions VIII. Dehalogenation with Hydrazine References 25 Miscellaneous Hydrogenolyses I. Allylic Oxygen II. Allylic Nitrogen III. Vinyl Functions IV. Debenzylation V. Hydrogenolysis of the Carbon-Carbon Bond VI. Hydrogenolysis of the Carbon-Oxygen Bond VII. Hydrogenolysis of the Carbon-Nitrogen Bond VIII. Hydrogenolysis of the Nitrogen-Oxygen Bond IX. Hydrogenolysis of the Oxygen-Oxygen Bond X. Hydrogenolysis of the Nitrogen-Nitrogen Bond ReferencesAuthor IndexSubject Index