Phase Transfer Catalysis in Organic Synthesis
The field of phase transfer catalysis is a tribute to the chemists involved in process development research. Phase transfer catalysis is a solution to numerous cost and yield problems encountered regularly in industrial laboratories. In fact, much of the early work in this area was conducted by indu...
Main Authors: | , |
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Format: | eBook |
Language: | English |
Published: |
Berlin, Heidelberg
Springer Berlin Heidelberg
1977, 1977
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Edition: | 1st ed. 1977 |
Series: | Reactivity and Structure: Concepts in Organic Chemistry
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Subjects: | |
Online Access: | |
Collection: | Springer Book Archives -2004 - Collection details see MPG.ReNa |
Table of Contents:
- 7.2 The Mechanism and General Features of the Cyanide Displacement Reaction
- 7.3 The Formation of Alkyl Cyanides
- 7.4 Formation of Acyl Nitriles
- 7.5 Synthesis of Cyanoformates
- 7.6 Cyanohydrin Formation
- 7.7 The Benzoin Condensation
- 7.8 Hydrocyanation, Cyanosilylation, and Other Reactions
- References
- 8. Reactions of Superoxide Ions
- 8.1 Introduction
- 8.2 Reactions at Saturated Carbon
- 8.3 Additions to Carbonyl Groups
- 8.4 Reactions With Aryl Halides
- References
- 9. Reactions of Other Nucleophiles
- 9.1 Introduction
- 9.2 Halide Ions
- 9.3 Azide Ions
- 9.4 Nucleophile Induced Elimination Reactions
- 9.5 Nitrite Ion
- 9.6 Hydrolysis Reactions
- 9.7 Anionic Polymerization Initiation
- 9.8 Organometallic Systems
- 9.9 Isotopic Exchange
- References
- 10. Alkylation Reactions
- 10.1 Introduction
- 10.2 The Substances Alkylated
- 10.3 Phase Transfer Alkylating Agents
- 10.4 Alkylation of Reissert’s Compound
- References
- 1. Introduction and Principles
- 1.1 Introduction
- 1.2 Early Examples
- 1.3 The Coalescence of Ideas
- 1.4 The Principle of Phase Transfer Catalysis
- 1.5 Evidence for the Mechanism of Phase Transfer Catalysis
- 1.6 Charged Catalysts: Quaternary Ions
- 1.7 Uncharged Catalysts: The Amines
- 1.8 Uncharged Catalysts: The Crown Ethers
- 1.9 Uncharged Catalysts: The Cryptands
- 1.10 Catalyst Comparisons
- 1.11 Solvents
- 1.12 The Role of Water in Phase Transfer Catalysis
- 1.13 Summary
- References
- 2. The Reaction of Dichlorocarbene With Olefins
- 2.1 Introduction
- 2.2 The Mechanism of the Dichlorocyclopropanation Reaction
- 2.3 Catalytic Cyclopropanation
- 2.4 Dichlorocyclopropanation of Simple Olefins
- 2.5 Cyclopropanation of Enamines
- 2.6 Dichlorocyclopropanation Followed by Rearrangement
- 2.7 Carbene Addition to Indoles
- 2.8 Carbene Addition to Furans and Thiophenes
- 2.9 Carbene Addition to Polycyclic Aromatics
- 14.4 Sulfur Stabilized Ylids
- References
- 15. Altered Reactivity
- 15.1 Introduction
- 15.2 Cation Effects
- 15.3 Affected Anions
- 15.4 Ambident Nucleophiles
- References
- 16. Addendum: Recent Developments in Phase Transfer Catalysis
- Author Index
- 11. Oxidation Reactions
- 11.1 Introduction
- 11.2 Permanganate Ion
- 11.3 Chromate Ion
- 11.4 Hypochlorite Ion
- 11.5 Catalytic Oxidation
- 11.6 Singlet Oxygen
- 11.7 Oxidation of Anions
- 11.8 Phosphorylation
- References
- 12. Reduction Techniques
- 12.1 Introduction
- 12.2 Borohydrides
- 12.3 Stoichiometric Reduction Systems
- 12.4 Other Catalytic Reductions
- 12.5 Altered Reactivity
- References
- 13. Preparation and Reactions of Sulfur Containing Substrates
- 13.1 Introduction
- 13.2 Preparation of Symmetrical Thioethers
- 13.3 Preparation of Mixed Sulfides
- 13.4 Preparation of Sulfides From Thiocyanates
- 13.5 Preparation of Alkylthiocyanates
- 13.6 Sulfides Resulting From Michael Additions
- 13.7 Synthesis of ?, ?-Unsaturated Sulfur Compounds
- 13.8 Other Phase Transfer Reactions of Sulfur Containing Substances
- References
- 14. Ylids
- 14.1 Introduction
- 14.2 Phase Transfer Wittig Reactions
- 14.3 The Wittig-Horner-Emmons Reaction
- 2.10 Carbene Addition to Conjugated Olefins
- 2.11 Michael Addition of the Trichloromethyl Anion
- 2.12 Dichlorocarbene Addition to Allylic Alcohols: A Cyclopentenone Synthon
- 2.13 Dichlorocarbene to Phenols: Reimer-Tiemann Reactions
- References
- 3. Reactions of Dichlorocarbene With Non-Olefinic Substrates
- 3.1 Introduction
- 3.2 C — H Insertion Reactions
- 3.3 Reaction With Alcohols: Synthesis of Chlorides
- 3.4 Carbene Addition to Imines
- 3.5 Addition to Primary Amines: Synthesis of Isonitriles..
- 3.6 Reaction With Hydrazine, Secondary, and Tertiary Amines
- 3.7 Dehydration With Dichlorocarbene
- 3.8 Miscellaneous Reactions of Dichlorocarbene
- References
- 4. Dibromocarbene and Other Carbenes
- 4.1 Introduction
- 4.2 Dibromocarbene Addition to Simple Olefins
- 4.3 Dibromocarbene Addition to Strained Alkenes
- 4.4 Dibromocarbene Addition toIndoles
- 4.5 Dibromocarbene Addition to Michael Acceptors
- 4.6 Other Reactions of Dibromocarbene
- 4.7 Other Halocarbenes
- 4.8 Phenylthio- and Phenylthio(chloro)carbene
- 4.9 Unsaturated Carbenes
- References
- 5. Synthesis of Ethers
- 5.1 Introduction
- 5.2 Mixed Ethers: The Mechanism
- 5.3 Rate Enhancement in the Williamson Reaction
- 5.4 Methylation
- 5.5 Phenyl Ethers
- 5.6 Methoxymethyl Ethers of Phenol
- 5.7 Diethers From Dihalomethanes
- 5.8 The Koenigs-Knorr Reaction
- 5.9 Epoxides
- References
- 6. Synthesis of Esters
- 6.1 Introduction
- 6.2 Tertiary Amines and Quaternary Ammonium Salts
- 6.3 Noncatalytic Esterification in the Presence of Ammonium Salts
- 6.4 Polycarbonate Formation
- 6.5 Crown Catalyzed Esterification
- 6.6 Crown Catalyzed Phenacyl Ester Synthesis
- 6.7 Crown Catalyzed Esterification of BOC-Amino Acid to Chloromethylated Resins
- 6.8 Cryptate and Resin Catalyzed Esterifications
- 6.9 Synthesis of Sulfonate and Phosphate Esters by PTC
- References
- 7. Reactions of Cyanide Ion
- 7.1 Introduction