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

Volume 33 of Science of Synthesis covers useful methods for the synthesis of Ene—X compounds, where X = S, Se, Te, N, and P. The reader will appreciate that a tremendous variety of compounds playing a central role in organic chemistry are included in this contribution. Substrates containing these functional groups serve as prominent and even archetypal electrophiles or nucleophiles in further synthetic transformations, and some are considered among the most important dienophiles in concerted cycloaddition reactions as well. Additionally, some of the functional groups included in this volume are playing an increasingly important role in molecules that possess significant biological activity.

The volume was ultimately divided into 46 discrete sections, divided unequally among the various atom types that comprise the focus of the volume. The seemingly endless variety of synthetic methods that can be utilized to approach the various substructures provides a serious challenge to anyone hoping to organize and select the best methods of synthesis of these materials, but this challenge has been met admirably by a dedicated and talented group of authors. I extend my sincere gratitude to these authors, who have devoted enormous effort to collect and critically analyze the primary literature concerning the synthesis of these classes of compounds. Their heroic efforts have made my job easy.

I would like to thank everyone who has assisted the effort at each and every point along the way. Thanks go to Dr. Joe Richmond who started me along the way in this odyssey, and was instrumental in establishing the outline of the volume. The support at Thieme has been incredible, and in particular I wish to extend my sincerest gratitude to Dr. Fiona Shortt de Hernandez, Dr. Colin Baillie, Dr. Mark Smith, and Dr. Marcus White for all of their advice and tremendous support.

Volume Editor

Gary A. Molander

Philadelphia, November 2006

Volume 33: Ene–X Compounds (X = S, Se, Te, N, P)

Preface

Volume Editor’s Preface

Table of Contents

Introduction

G. A. Molander

33.1 Product Class 1: Alk-1-enyl Sulfur Compounds

33.1.1 Product Subclass 1: Alk-1-enesulfonic Acids and Derivatives

J. C. Carretero and R. G. Arrayás

33.1.2 Product Subclass 2: Alk-1-enyl Sulfones

J. C. Carretero and R. G. Arrayás

33.1.3 Product Subclass 3: S-Alk-1-enylsulfoximides

J. C. Carretero and R. G. Arrayás

33.1.4 Product Subclass 4: Alk-1-enesulfinic Acids and Derivatives

J. C. Carretero and R. G. Arrayás

33.1.5 Product Subclass 5: Alk-1-enyl Sulfoxides, Sulfimides, and Related Compounds

J. C. Carretero and R. G. Arrayás

33.1.6 Product Subclass 6: Alk-1-enethiols

J. Drabowicz, P. Kie∤basiński, and M. Miko∤ajczyk

33.1.7 Product Subclass 7: Metal Alk-1-enethiolates

J. Drabowicz, P. Kie∤basiński, and M. Miko∤ajczyk

33.1.8 Product Subclass 8: Alk-1-enyl Sulfides

J. Drabowicz, P. Kie∤basiński, and M. Miko∤ajczyk

33.1.9 Product Subclass 9: Alk-1-enylsulfonium Salts

J. Drabowicz, P. Kie∤basiński, and M. Miko∤ajczyk

33.1.10 Product Subclass 10: Alk-1-enesulfenic Acid Derivatives

J. Drabowicz, P. Kie∤basiński, and M. Miko∤ajczyk

33.1.11 Product Subclass 11: Alk-1-enyl Disulfides

J. Drabowicz, P. Kietbasiński, and M. Miko∤ajczyk

33.1.12 Product Subclass 12: Thietes and Derivatives

E. Block

33.1.13 Product Subclass 13: 2,3-Dihydrothiophenes and Derivatives

E. Block

33.1.14 Product Subclass 14: 3,4-Dihydro-2H-thiopyrans and Derivatives

E. Block

33.1.15 Product Subclass 15: 2,3,4,5-Tetrahydrothiepins, Larger Rings, and Derivatives

E. Block

33.2 Product Class 2: Alk-1-enyl Selenium Compounds

D. Avilov and D. Dittmer

33.3 Product Class 3: Alk-1-enyl Tellurium Compounds

D. Avilov and D. Dittmer

33.4 Product Class 4: Alk-1-enyl Nitrogen Compounds

33.4.1 Product Subclass 1: 1-Nitroalkenes

N. Ono

33.4.2 Product Subclass 2: 1-Nitrosoalkenes

H.-U. Reissig and R. Zimmer

33.4.3 Product Subclass 3: N-Alk-1-enyliminosulfur Compounds

H.-U. Reissig and R. Zimmer

33.4.4 Product Subclass 4: Alk-1-enediazonium Salts, Alkeneazoxy, and Alkeneazo Compounds

33.4.5 Product Subclass 5: N-Alk-1-enyliminophosphorus Compounds

H.-U. Reissig and R. Zimmer

33.4.6 Product Subclass 6: Enamines

T. Sammakia, J. A. Abramite, and M. F. Sammons

33.4.7 Product Subclass 7: Enammonium Salts

T. Sammakia, J. A. Abramite, and M. F. Sammons

33.4.8 Product Subclass 8: N-Silylenamines

S. J. Collier

33.4.9 Product Subclass 9: N-Borylenamines

S. J. Collier

33.4.10 Product Subclass 10: N-Haloenamines

S. J. Collier

33.4.11 Product Subclass 11: N-Alk-1-enylhydroxylamines

S. J. Collier

33.4.12 Product Subclass 12: N-Alk-1-enylaminosulfur Compounds

S. J. Collier

33.4.13 Product Subclass 13: Alk-1-enylhydrazines

S. J. Collier and M. D. McLaws

33.4.14 Product Subclass 14: Alk-1-enyl Azides

S. J. Collier

33.4.15 Product Subclass 15: N-Alk-1-enylaminophosphorus Compounds

S. J. Collier

33.4.16 Product Subclass 16: 1,2-Dihydroazetes and Derivatives

P. Jubault, E. Leclerc, and J.-C. Quirion

33.4.17 Product Subclass 17: 2,3-Dihydro-1H-pyrroles and Derivatives

P. Jubault, E. Leclerc, and J.-C. Quirion

33.4.18 Product Subclass 18: 1,2-Dihydropyridines, 1,4-Dihydropyridines, and Derivatives

J.-C. Quirion, E. Leclerc, and P. Jubault

33.4.19 Product Subclass 19: 1,2,3,4-Tetrahydropyridines and Derivatives

J.-C. Quirion

33.4.20 Product Subclass 20: 2,3,4,5-Tetrahydro-1H-azepines, Larger Rings, and Derivatives

J.-C. Quirion, E. Leclerc, and P. Jubault

33.5 Product Class 5: Alk-1-enyl Phosphorus Compounds

33.5.1 Product Subclass 1: Alk-1-enylphosphonic Acids and Derivatives

A. C. Gaumont and M. Gulea

33.5.2 Product Subclass 2: Alk-1-enylphosphinic Acids and Derivatives

A. C. Gaumont and M. Gulea

33.5.3 Product Subclass 3: Alk-1-enylphosphine Oxides and Derivatives

A. C. Gaumont and M. Gulea

33.5.4 Product Subclass 4: Alk-1-enylphosphines

A. C. Gaumont and M. Gulea

33.5.5 Product Subclass 5: Alk-1-enylphosphonium Salts

A. C. Gaumont and M. Gulea

33.5.6 Product Subclass 6: P-Heteroatom-Substituted Alk-1-enylphosphines

A. C. Gaumont and M. Gulea

33.5.7 Product Subclass 7: 1,2-Dihydrophosphetes and Derivatives

Gy. Keglevich and H. Szelke

33.5.8 Product Subclass 8: 2,3-Dihydro-1H-phospholes and Derivatives

Gy. Keglevich and H. Szelke

33.5.9 Product Subclass 9: 1,2,3,4-Tetrahydrophosphinines and Derivatives

Gy. Keglevich and H. Szelke

33.5.10 Product Subclass 10: 1,4-Dihydrophosphinines and Derivatives

Gy. Keglevich and H. Szelke

Keyword Index

Author Index

Abbreviations

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!

Lesen Sie weiter in der vollständigen Ausgabe!