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.

November 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 is the third in Hetarenes and Related Ring Systems (Category 2) of Science of Synthesis and deals with five-membered hetarenes with one chalcogen and one additional heteroatom. Throughout this category, a hetarene is considered to be a heterocyclic ring with a fully conjugated perimeter of π- or nonbonding electrons. Also, potentially tautomeric systems with a hydroxy, sulfanyl, or amino substituent are included when conjugation is possible at least in one tautomer. In the present volume, this formal definition leads to quite different types of five-membered heterocyclic ring systems including the 1,2- or 1,3-arrangement of two chalcogen atoms to give cationic rings, as well as 1,2- or 1,3- combinations of a chalcogen atom and a nitrogen or phosphorus atom. The latter group comprises well-known ring systems such as oxazoles or thiazoles, but also less well-studied ring systems.

In each case, not only monocyclic rings are considered but also annulated derivatives, in particular benzoannulated systems, and other examples of arenoannulation and also hetarenoannulation. When convenient, syntheses of these derivatives are covered together with the chemistry of the monocycles, otherwise they immediately follow the chapter on the corresponding monocyclic system. A separate chapter is devoted to the chemistry of tri- or tetraheterapentalenes, which have a particularly interesting electronic structure.

Special thanks are due to the many authors of this volume who critically considered a vast amount of material and selected the most important synthetic methods. To some extent, the information of Houben–Weyl, Vols. E 8a and E 8b could be used, but those volumes were published in German and with a less-vigorous organizational scheme. It should be especially acknowledged that the authors patiently followed the changes in the formal presentation which had to be implemented while work on this volume was already in progress.

Throughout the development of this volume, it was a pleasure to cooperate with the publishing house in Stuttgart and in particular with Dr. Fiona Shortt and her team, who were always ready to help and have done a great job in securing the quality of this volume.

Clausthal-Zellerfeld, November 2001

Volume Editor

Ernst Schaumann

Volume 11: Five-Membered Hetarenes with One Chalcogen and One Additional Heteroatom

Preface

Volume Editor’s Preface

Table of Contents

Introduction

E. Schaumann

11.1 Product Class 1:1,3-Dioxolium Salts and Annulated Analogues

H. Perst

11.2 Product Class 2:1,2-Oxathiolium Salts

H. Perst

11.3 Product Class 3:1,3-Oxathiolium Salts and Related Compounds

H. Perst and C. Klenke

11.4 Product Class 4:1,2-Oxaselenolium Salts

H. Perst

11.5 Product Class 5:1,3-Oxaselenolium Salts

H. Perst

11.6 Product Class 6:1,2-Oxatellurolium Compounds and Benzoannulated Analogues

H. Perst

11.7 Product Class 7:1,2-Dithiolium Salts and Related Compounds

C. Th. Pedersen

11.8 Product Class 8:1,3-Dithiolium Salts, Se and Te Analogues, and Benzoannulated Analogues

G. Schukat and E. Fanghänel

11.9 Product Class 9: Isoxazoles

B. J. Wakefield

11.10 Product Class 10: 1,2-Benzisoxazoles and Related Compounds

R. K. Smalley

11.11 Product Class 11: 2,1-Benzisoxazoles and Related Compounds

R. K. Smalley

11.12 Product Class 12: Oxazoles

G. V. Boyd

11.13 Product Class 13: Benzoxazoles and Other Annulated Oxazoles

G. V. Boyd

11.14 Product Class 14:1,3-Oxaphospholes and Benzoannulated Analogues

D. Gudat

11.15 Product Class 15: Isothiazoles

D. W. Brown and M. Sainsbury

11.16 Product Class 16: Benzisothiazoles

D. W. Brown and M. Sainsbury

11.17 Product Class 17: Thiazoles

D. Kikelj and U. Urleb

11.18 Product Class 18: Benzothiazoles and Related Compounds

H. Ulrich

11.19 Product Class 19:1,2- and 1,3-Thiaphospholes and Benzoannulated Analogues

D. Gudat

11.20 Product Class 20: Isoselenazoles

W.-D. Pfeiffer

11.21 Product Class 21: Annulated Isoselenazole Compounds

W.-D. Pfeiffer

11.22 Product Class 22: Selenazoles

W.-D. Pfeiffer

11.23 Product Class 23: Annulated Selenazole Compounds

W.-D. Pfeiffer

11.24 Product Class 24:1,3-Selenaphospholes

D. Gudat

11.25 Product Class 25: Isotellurazoles, and Annulated Isotellurazole and Tellurazole Compounds W.-D. Pfeiffer

Keyword Index

Author Index

Abbreviations

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