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Table Of Contents

1.1. Introduction
1.2. Hydrogenation Catalysts
1.3. Choosing a Catalyst
1.4. Choosing a Catalyst Support
1.5. Choosing a Metal Concentration
1.6. Choosing Conditions
1.7. Effect of Temperature
1.8. Prereduction
1.9. Measurement of Selectivity
1.10. Catalyst Reuse
1.11. Synergism
1.12. Solvents
1.12.1. Influence of Solvent on Selectivity
1.12.2. Effect of Acidity
1.12.3. Reactive Solvents
1.13. Safety
1.13.1. Catalysts
1.13.2. Loading a Catalyst
1.14. HOMOGENEOUSCATALYSTS 13
1.14. Homogeneous Catalysts
1.14.1 Asymmetric Hydrogenation
1.14.2. Ligand Synthesis
1.14.3. Chiral Homogeneous Hydrogenations
1.15. Hydrogen-Transfer Reductions
1.16. HYDROGENATION REACTORS 17
1.16. Hydrogenation Reactors
1.16.1. Atmospheric Pressure Reactors
1.16.2. Low-Pressure Reactors
1.16.3. High-Pressure Reactors
1.16.3.1. safety
1.17. Catalyst Preparation
1.17.1. Purchased Catalysts
1.18.1. Cost of Catalyst
1.18.2. Catalyst Life
1.18.3. Space-Time Yield
1.18.4. Actual Yield
2.1. Double-Bond Migration
2.1.1. Mechanism of Olefin Hydrogenation
2.1.2. Effect of Hydrogen Availability
2.1.3. Catalysts
2.1.4. Effect of Solvent
2.2. Consequences of Double-Bond Migration
2.3.1. Dienes and Polyenes
2.3.2. Unsaturated Carbonyl Compounds
2.4. VINYLIC AND ALLYLIC FUNCTIONS 41
2.4. Vinylic and Allylic Functions
2.5. Olefinic Sulfur Compounds
2.6. Stereochemistry
2.6.1. Asymmetric Hydrogenation of Olefins
3.1. Catalysts
3.4. Functionalized Acetylenes
3.4.1. Acetylenic Carbinols, Glycols, and Esters
3.4.2. Acetylenic Epoxides
3.4.3. Propagargylamines
3.4.4. Acetylenic Aldehydes and Ketones
4.1. Catalysts
4.2. Solvents
4.2.1. Alcohol Solvents
4.3. Hydrogenolysis
4.3.1. Aliphatic Carbonyls
4.3.2. Aromatic Carbonyls
4.4. Unsaturated Carbonyls
4.5. Diketones
4.6. Stereochemistry
4.6.1. Axial Alcohols
4.6.2. Asymmetric Hydrogenation
5.1. Acids
5.2. ANHYDRIDES 79
5.2. Anhydrides
5.3. Esters
6.1. Introduction
6.2. Catalysts
6.3. Solvents
6.4. Amine and Carbonyl Precursors
REFERENCES
6.5. Stereochemistry
7.1. Nitriles
7.1.1. Solvents
7.1.2. Catalysts
7.1.3. Cyclizations
1.2. Oximes
7.2.1. Catalysts
7.2.2. Solvents
7.2.3. Oximino Ketones
References
8.1. Catalysts
8.3. INFLUENCE OF IMPURITIES 105
8.3. Influence of Impurities
8.4. Aromatic Hydroxylamines
8.4.1. Cyclic Products
8.5. Bifunctional Molecules
8.5.1. Halonitro Aromatics
8.5.2. Acetylenic and Olefinic Nitro Compounds
8.5.4. Nitroaldehydes and Nitroketones
8.5.6. Nitroenamines
9.1. Catalysts
9.2. Olefin Intermediates
9.3. EFFECT OF SUBSTRATE STRUCTURE 119
9.3. Effect of Substrate Structure
9.3.1. Polycyclic Systems
9.3.2. Fused Rings
10.1. Anilines
10.1.1. Catalysts
10.1.2. Catalyst Reactivation
10.1.3. Control of Coupling
10.1.4. Reductive Hydrolysis
10.1.5. Synthetic Applications
10.2. Phenols and Derivatives
10.2.1. Partial Hydrogenation of Phenols to Cyclohexanones
10.2.2. Deoxygenation with Ring Saturation
11.1. Ring Saturation
11.1.1. Furans
11.1.2. Pyrroles
11.1.3. Indoles
11.1.4. Pyridines and Derivatives
11.1.4.1. Partial Hydrogenation
11.2. RING HYDROGENOLYSIS 137
11.1.4.2. Decarboxylation
11.2. Ring Hydrogenolysis
11.2.1 Oxiranes
11.2.1.1. Deoxygenation
11.2.1.2. Direction of Ring Opening
11.2.2. Aziridines
11.2.3. Isoxazoles
11.2.4. Isoxazolines
12.2. Basic and Acidic Media
12.3. Poly halo Compounds
12.4. Halonitro Compounds
12.5. Coupling Reactions
12.6. Rosenmund Reduction
12.6.1. Regulated Catalysts
12.6.2. Procedure
13.1. Benzyl Groups Attached to Oxygen
13.1.1. Effect of Substrate Structure
13.1.2. Promoters
13.1.3. Stereochemistry of Hydrogenolysis
13.1.4. Carbobenzyloxy Compounds
13.2. BENZYL GROUPS ATTACHED TO NITROGEN 163
13.2. Benzyl Groups Attached to Nitrogen
13.2.1. Catalysts
13.2.2. Effect of Structure
13.2.3. Stereochemistry
13.3. VINYL FUNCTIONS 165
13.2.4. Reverse Selectivity
13.3. Vinyl Functions
13.4. ALLYLIC FUNCTIONS 167
13.4. Allylic Functions
13.4.1. Steric Factors
13.4.2. Catalysts and Environment
13.4.3. Double-Bond Migration
13.5. Hydrogenolysis of the Nitrogen-Nitrogen Bond
13.5.1. Hydrazones and Hydrazides
13.5.2. Azines
13.5.3. Azides
13.6. HYDROGENOLYSIS OF THE NITROGEN-OXYGEN BOND 171
13.6. Hydrogenolysis of the Nitrogen-Oxygen Bond
13.6.1. Amine Oxides
13.6.2. Hydroxylamines
13.7. HYDROGENOLYSIS OF THE CARBON-CARBON BOND 173
13.6.3. N-Nitrosoamines
13.6.4. C-Nitroso Compounds
13.7. Hydrogenolysis of the Carbon-Carbon Bond
13J.1. Cyclopropanes
13.7.2. Cyclobutanes
13.7.3 Aromatization
13.8. Hydrogenolysis of the Oxygen-Oxygen Bond
186 INDEX OF COMPOUNDS AND METHODS
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12290306 Hydrogenation Methods Paul N Rylander 1985

12290306 Hydrogenation Methods Paul N Rylander 1985

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