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Catalytic Hydrogenation in Organic Syntheses - 1st Edition - ISBN: 9780126053555, 9780323138536

Catalytic Hydrogenation in Organic Syntheses

1st Edition

Author: Rylander
eBook ISBN: 9780323138536
Imprint: Academic Press
Published Date: 28th August 1979
Page Count: 336
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Catalytic Hydrogenation in Organic Syntheses focuses on the process of catalytic hydrogenation in organic synthesis. This book gives the reader easy access to catalytic history, to show what can be done and how to do it. A variety of working generalities and common sense guides are given as aids in selecting catalytic metal, catalyst support, concentration of metal and catalyst, solvent, and reaction conditions. All manner of hydrogenation catalysts are considered and mechanisms of hydrogenation are presented at a level that is useful to the synthetic organic chemist. This volume is comprised of 15 chapters and begins with an overview of catalytic hydrogenation and heterogeneous hydrogenation catalysts, along with hydrogenation reactors and reaction conditions. The discussion then shifts to the hydrogenation of compounds such as acetylenes, olefins, aldehydes, ketones, nitriles, oximes, acids, esters, lactones, anhydrides, and nitro compounds as well as carbocyclic aromatics and heterocyclic compounds. The reader is also introduced to reductive alkylation, catalytic dehydrohalogenation, and hydrogenolysis of small rings. A chapter on miscellaneous hydrogenolyses concludes the book. This book will be of interest to organic chemists working in the field of catalytic hydrogenation.

Table of Contents


Chapter 1 Hydrogenation Catalysts, Reactors, and Reaction Conditions

I. General Considerations

II. Reaction Conditions and Catalyst Variables

III. Hydrogenation Reactors

IV. Preparation of Catalysts


Chapter 2 Hydrogenation of Acetylenes

I. General Considerations

II. Catalysts

III. Acetylenic Carbinols and Glycols

IV. Hydrogenolysis

V. Acetylenic Aldehydes and Ketones

VI. Polyacetylenes


Chapter 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


Chapter 4 Hydrogenation of Acids, Esters, Lactones, and Anhydrides

I. Hydrogenation of Acids

II. Hydrogenolysis of Esters

III. Hydrogenation of Lactones

IV. Hydrogenation of Anhydrides


Chapter 5 Hydrogenation of Aldehydes

I. Saturated Aliphatic Aldehydes

II. Unsaturated Aliphatic Aldehydes

III. Aromatic Aldehydes

IV. Aromatic Unsaturated Aldehydes


Chapter 6 Hydrogenation of Ketones

I. Aliphatic Ketones

II. Aromatic Ketones


Chapter 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


Chapter 8 Hydrogenation of Nitriles

I. Mechanism

II. Catalysts

III. Unsymmetrical Amines

IV. Cyclizations

V. Reductive Hydrolysis

VI. Methylation


Chapter 9 Hydrogenation of Oximes

I. Catalysts

II. Substrates

III. Solvent

IV. Products of Partial Reduction

V. Products of Hydrolysis

VI. Bifunctional Molecules

VII. Stereochemistry


Chapter 10 Reductive Alkylation

I. Substrates

II. Catalysts

III. Stereochemistry


Chapter 11 Hydrogenation of Carbocyclic Aromatics

I. Carbocyclic Aromatics

II. Anilines

III. Phenols and Phenyl Ethers


Chapter 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


Chapter 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


Chapter 14 Hydrogenolysis of Small Rings

I. Cyclopropanes

II. Oxiranes

III. Aziridines


Chapter 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




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© Academic Press 1979
28th August 1979
Academic Press
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