Catalytic Hydrogenation in Organic Syntheses

Catalytic Hydrogenation in Organic Syntheses

1st Edition - August 28, 1979

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  • Author: Rylander
  • eBook ISBN: 9780323138536

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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

  • Preface

    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



Product details

  • No. of pages: 336
  • Language: English
  • Copyright: © Academic Press 1979
  • Published: August 28, 1979
  • Imprint: Academic Press
  • eBook ISBN: 9780323138536

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