Phase Transfer Catalysis in Organic Synthesis

1. Front Matter

   Pages I-XV

   PDF

2. Introduction and Principles

   • William P. Weber, George W. Gokel

   Pages 1-17

3. The Reaction of Dichlorocarbene With Olefins

   • William P. Weber, George W. Gokel

   Pages 18-43

4. Reactions of Dichlorocarbene With Non-Olefinic Substrates

   • William P. Weber, George W. Gokel

   Pages 44-57

5. Dibromocarbene and Other Carbenes

   • William P. Weber, George W. Gokel

   Pages 58-72

6. Synthesis of Ethers

   • William P. Weber, George W. Gokel

   Pages 73-84

7. Synthesis of Esters

   • William P. Weber, George W. Gokel

   Pages 85-95

8. Reactions of Cyanide Ion

   • William P. Weber, George W. Gokel

   Pages 96-108

9. Reactions of Superoxide Ions

   • William P. Weber, George W. Gokel

   Pages 109-116

10. Reactions of Other Nucleophiles

    • William P. Weber, George W. Gokel

    Pages 117-135

11. Alkylation Reactions

    • William P. Weber, George W. Gokel

    Pages 136-205

12. Oxidation Reactions

    • William P. Weber, George W. Gokel

    Pages 206-214

13. Reduction Techniques

    • William P. Weber, George W. Gokel

    Pages 215-220

14. Preparation and Reactions of Sulfur Containing Substrates

    • William P. Weber, George W. Gokel

    Pages 221-233

15. Ylids

    • William P. Weber, George W. Gokel

    Pages 234-241

16. Altered Reactivity

    • William P. Weber, George W. Gokel

    Pages 242-251

17. Addendum: Recent Developments in Phase Transfer Catalysis

    • William P. Weber, George W. Gokel

    Pages 252-266

18. Back Matter

    Pages 267-280

    PDF

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 industrial chemists although the work was not labelled phase transfer catalysis at the time. We certainly do not intend to minimize the contributions of academic chemists to this field, but it is an unalterable fact that much of the early understanding and many of the early advances came from industrial laboratories. A special tribute is due to Dr. Charles Starks of the Continental Oil Company. By the mid sixties, Starks had formulated the principles of phase transfer catalysis and had applied for patents on many reactions that others were later to examine in somewhat greater detail. His mechanistic model of phase transfer catalysis still stands up well today and is a model for much of the thinking in this area. It is fitting that Starks suggested the name "phase transfer catalysis" by which the whole field is now known. We wish to thank a number of people who have aided us in many ways in the preparation of this volume. We very much appreciate the helpful discussions and insights provided by Drs. Henry Stevens and Andrew Kaman of PPG Industries in Barberton, Ohio. We also thank Dr. L. A.

• Alkene
• Amine
• Ether
• Phenol
• Weber
• aromatic
• carbon
• catalysis
• nucleophile
• organic synthesis
• oxygen
• polymer
• rearrangement
• synthesis

• Department of Chemistry, University of Southern California, University Park, Los Angeles, USA

  William P. Weber

• Department of Chemistry, 152 Davey Laboratory, The Pennsylvania State University, University Park, USA

  George W. Gokel

Policies and ethics