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 is concerned with six-membered hetarenes with one chalcogen, i.e. pyrylium salts and pyranones together with their sulfur, selenium, and tellurium analogues. As with other volumes of Science of Synthesis, it is the synthesis of these hetarenes which is the dominant topic; their chemistry is covered only when relevant to their synthesis, or in a few instances where it leads to generally useful synthetic procedures, e.g. the Diels–Alder chemistry of pyran-2-ones.

The chemistry of pyrylium salts and pyranones has been studied for a very long time, indeed since the beginning of modern organic chemistry. Hence, many of the references included in this volume date back to fairly early work, although the literature coverage continues up to the end of 2002. However, both pyranones and pyrylium salts retain considerable industrial interest up to the present day, the former because of their biological activities and the latter owing to their use as dyes. So despite their age, the compound classes covered in this volume are of considerable contemporary interest and are likely to remain so for many years to come.

The structure of this volume follows that established in the other hetarene volumes of Science of Synthesis, i.e. the material is organised into methods for the synthesis of the product class in question, with each method usually including a discussion of the scope of the method, examples, and an experimental procedure. The product classes are ordered according to the Science of Synthesis guidelines, with the methods and variations within each product class following the sequence: synthesis by ring-closure reactions, synthesis by ring transformation, aromatization, and synthesis by substituent modification.

Finally, I should like to thank everyone who has contributed to this volume, in particular Dr. Joe P. Richmond for his help at the planning stage, and the authors for all their hard work in putting it together. Finally, I gratefully acknowledge the unstinting efforts of Dr. M. Fiona Shortt de Hernandez and her team at Thieme for their support, patience, and hard work during the course of this project and for their tolerance of my brinksmanship.

Volume Editor

E. J. Thomas

Manchester, July 2003

Volume 14: Six-Membered Hetarenes with One Chalcogen

Preface

Volume Editor’s Preface

Table of Contents

Introduction

E. J. Thomas

14.1 Product Class 1: Pyrylium Salts

T. S. Balaban and A. T. Balaban

14.2 Product Class 2: Benzopyrylium Salts

M. Nógrádi

14.3 Product Class 3: Pyranones and Pyranthiones

K. Afarinkia and V. Vinader

14.4 Product Class 4: Benzopyranones and Benzopyranthiones

A. C. Williams and N. Camp

14.5 Product Class 5:3-Oxidopyrylium Salts and Their Thio and Benzo-Fused Analogues

A. Nelson

14.6 Product Class 6: Thiopyrylium Salts

W.-D. Rudorf

14.7 Product Class 7: Benzothiopyrylium Salts

W.-D. Rudorf

14.8 Product Class 8: Thiopyranones and Thiopyranthiones

S. Faulkner, R. C. Whitehead, and R. J. Aarons

14.9 Product Class 9: Benzothiopyranones and Benzothiopyranthiones

A. Nelson

14.10 Product Class 10: Selenopyrylium and Benzoselenopyrylium Salts

P. J. Murphy

14.11 Product Class 11: Selenopyranones and Benzoselenopyranones

P. J. Murphy

14.12 Product Class 12: Telluropyrylium and Benzotelluropyrylium Salts

P. J. Murphy

14.13 Product Class 13: Telluropyranones and Benzotelluropyranones

P. J. Murphy

Keyword Index

Author Index

Abbreviations

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Lesen Sie weiter in der vollständigen Ausgabe!

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