
Catalytic Hydrogenation in Organic Syntheses
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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
References
Chapter 2 Hydrogenation of Acetylenes
I. General Considerations
II. Catalysts
III. Acetylenic Carbinols and Glycols
IV. Hydrogenolysis
V. Acetylenic Aldehydes and Ketones
VI. Polyacetylenes
References
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
References
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
References
Chapter 5 Hydrogenation of Aldehydes
I. Saturated Aliphatic Aldehydes
II. Unsaturated Aliphatic Aldehydes
III. Aromatic Aldehydes
IV. Aromatic Unsaturated Aldehydes
References
Chapter 6 Hydrogenation of Ketones
I. Aliphatic Ketones
II. Aromatic Ketones
References
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
References
Chapter 8 Hydrogenation of Nitriles
I. Mechanism
II. Catalysts
III. Unsymmetrical Amines
IV. Cyclizations
V. Reductive Hydrolysis
VI. Methylation
References
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
References
Chapter 10 Reductive Alkylation
I. Substrates
II. Catalysts
III. Stereochemistry
References
Chapter 11 Hydrogenation of Carbocyclic Aromatics
I. Carbocyclic Aromatics
II. Anilines
III. Phenols and Phenyl Ethers
References
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
References
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
References
Chapter 14 Hydrogenolysis of Small Rings
I. Cyclopropanes
II. Oxiranes
III. Aziridines
References
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
References
Index
Product details
- No. of pages: 336
- Language: English
- Copyright: © Academic Press 1979
- Published: August 28, 1979
- Imprint: Academic Press
- eBook ISBN: 9780323138536
About the Author
Rylander
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