Science of Synthesis

Science of Synthesis is the authoritative and comprehensive reference work for the entire field of organic and organometallic synthesis.

Science of Synthesis presents the important synthetic methods for all classes of compounds and includes:

Methods critically evaluated by leading scientists

Background information and detailed experimental procedures

Schemes and tables which illustrate the reaction scope

Preface

As our understanding of the natural world increases, we begin to understand complex phenomena at molecular levels. This level of understanding allows for the design of molecular entities for functions ranging from material science to biology. Such design requires synthesis and, as the structures increase in complexity as a necessity for specificity, puts increasing demands on the level of sophistication of the synthetic methods. Such needs stimulate the improvement of existing methods and, more importantly, the development of new methods. As scientists confront the synthetic problems posed by the molecular targets, they require access to a source of reliable synthetic information. Thus, the need for a new, comprehensive, and critical treatment of synthetic chemistry has become apparent. To meet this challenge, an entirely new edition of the esteemed reference work Houben–Weyl Methods of Organic Chemistry will be published starting in the year 2000.

To reflect the new broader need and focus, this new edition has a new title, Science of Synthesis, Houben–Weyl Methods of Molecular Transformations. Science of Synthesis will benefit from more than 90 years of experience and will continue the tradition of excellence in publishing synthetic chemistry reference works. Science of Synthesis will be a balanced and critical reference work produced by the collaborative efforts of chemists, from both industry and academia, selected by the editorial board. All published results from journals, books, and patent literature from the early 1800s until the year of publication will be considered by our authors, who are among the leading experts in their field. The 48 volumes of Science of Synthesis will provide chemists with the most reliable methods to solve their synthesis problems. Science of Synthesis will be updated periodically and will become a prime source of information for chemists in the 21st century.

Science of Synthesis will be organized in a logical hierarchical system based on the target molecule to be synthesized. The critical coverage of methods will be supported by information intended to help the user choose the most suitable method for their application, thus providing a strong foundation from which to develop a successful synthetic route. Within each category of product, illuminating background information such as history, nomenclature, structure, stability, reactivity, properties, safety, and environmental aspects will be discussed along with a detailed selection of reliable methods. Each method and variation will be accompanied by reaction schemes, tables of examples, experimental procedures, and a background discussion of the scope and limitations of the reaction described.

The policy of the editorial board is to make Science of Synthesis the ultimate tool for the synthetic chemist in the 21st century.

We would like to thank all of our authors for submitting contributions of such outstanding quality, and, also for the dedication and commitment they have shown throughout the entire editorial process.

October 2000

The Editorial Board

D. Bellus (Basel, Switzerland)

E. N. Jacobsen (Cambridge, USA)

S. V. Ley (Cambridge, UK)

R. Noyori (Nagoya, Japan)

M. Regitz (Kaiserslautern, Germany)

P. J. Reider (New Jersey, USA)

E. Schaumann (Clausthal-Zellerfeld, Germany)

I. Shinkai (Tsukuba, Japan)

E. J. Thomas (Manchester, UK)

B. M. Trost (Stanford, USA)

Volume Editor’s Preface

This volume of Science of Synthesis covers compounds containing two carbon–hetero-atom bonds. These heteroatom analogues of aldehydes and ketones are extensively used for the synthesis of complex organic molecules and thus have been studied for a very long period of time. The book consists of 23 chapters that discuss the different functional groups of interest. The pattern in which each chapter is covered follows a regular plan ordered according to Science of Synthesis guidelines. First, there is a general equation illustrating various approaches toward the synthesis of the particular functional group being reviewed. Each reaction is discussed with emphasis on its particular value and limitations. A limited amount of background and theory is often included, not only to account for the path that the reaction takes, but also for its limitations and any byproducts formed. Finally, examples are given, many in sufficient detail to permit preparation in the laboratory and others to illustrate minor variations not necessarily presented in the discussion. Treatment is both selective and critical, the most important fact desired is the preferred methods of synthesis of a particular functional group.

Emphasis is placed on providing recent references, since the original synthetic method may have been improved. Some references are included as benchmark papers and others for their historical interest. Many review references are also included. With the explosive growth of synthetic organic chemistry still continuing, it is impossible to avoid omissions. Each author is an authority in the field and references are provided through 2003. The best synthetic methods available as well as additional information on the scope and limitations of each functional group are nicely summarized by this group of experts.

A number of people must be thanked for their contributions and help in completing this project. I am grateful to Dr. Joe P. Richmond for his assistance in the planning stage, Dr. Daniel Bellus for his support and encouragement, the authors for all their hard work in putting the book together, and finally Dr. M. Fiona Shortt de Hernandez and her capable team at Thieme for their support and constructive input.

Atlanta, April 2004

Volume Editor

Albert Padwa

Volume 26: Ketones

Preface

Volume Editors’ Preface

Table of Contents

Introduction

A. Padwa

27.1 Product Class 1: Sulfur Ylides

V. Aggarwal and J. Richardson

27.2 Product Class 2: Alkvlidenesulfonium Salts or α-Sulfanvl Carbocations

C. O. Kappe

27.3 Product Class 3: Thioaldehyde and Thioketone 5,5-Dioxides and Oxyimides (Sulfenes and Derivatives)

B. Zwanenburg

27.4 Product Class 4: Thioaldehyde and Thioketone 5-Oxides and 5-Imides (Sulfines and Derivatives)

B. Zwanenburg

27.5 Product Class 5: Thioaldehydes

S. J. Collier

27.6 Product Class 6: Thioketones

M. J. Dabdoub

27.7 Product Class 7: Imines

K. Abbaspour Tehrani and N. De Kimpe

27.8 Product Class 8: Iminium Salts

K. Abbaspour Tehrani and N. De Kimpe

27.9 Product Class 9: N-Acylimines

L. Fisera

27.10 Product Class 10: N-Acyliminium Salts

R. A. Pilli and G. B. Rosso

27.11 Product Class 11: Azomethine Ylides

W. Eberbach

27.12 Product Class 12: N-Haloimines

Jie Jack Li

27.13 Product Class 13: Nitrones and Cyclic Analogues

P. Merino

27.14 Product Class 14: Nitronic Acids and Their Derivatives

Jie Jack Li

27.15 Product Class 15: Oximes

M. Yamane and K. Narasaka

27.16 Product Class 16: Azines

D. M. Wilson and Y. Zhang

27.17 Product Class 17: Hydrazones

S. Kim and J.-Y. Yoon

27.18 Product Class 18: Hydrazonium Compounds

Y. Zhang and D. M. Wilson

27.19 Product Class 19: Azomethine Imines

J. G. Schantl

27.20 Product Class 20: N-Nitroimines and N-Nitrosoimines

Jie Jack Li

27.21 Product Class 21: Diazo Compounds

H. Heydt

27.22 Product Class 22: Alkylidenephosphines

E. Niecke, A. Ruban, and M. Raab

27.23 Product Class 23: Alkylidenephosphonium Salts

E. Niecke, A. Ruban, and M. Raab ■

27.24 Product Class 24: Alkylidenephosphoranes

R. Schobert and G. J. Gordon

Keyword Index

Author Index

Abbreviations

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