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

Houben–Weyl Methods of Organic Chemistry has nearly 100 years of history. Numerous synthetic methods described in the hitherto published Houben–Weyl series have greatly contributed to the development of organic chemistry and related fields. On the other hand, dramatic developments in organometallic chemistry during the past few decades have provided a large number of new organometallic reagents useful for organic transformations and have greatly promoted the development of synthetic organic chemistry. This scientific progress and the increasing importance of organometallic complexes in synthesis are clearly reflected in the new series, Science of Synthesis, Houben–Weyl Methods of Molecular Transformations. Thus, organometallics occupies a considerably large part consisting of eight volumes in Category 1 of this new series. Among them, this volume deals with organometallic complexes of groups 7-3 covering Mn, Tc, Re, Cr, Mo, W, V, Nb, Ta, Ti, Zr, Hf, Sc, Y, lanthanides, and actinides. It constitutes the second volume in the organometallics category and the second volume of the Science of Synthesis series.

The elements of groups 7-3 as well as other metallic elements provide numerous organometallic complexes that present a variety of bonding styles and molecular structures. Although these complexes exhibit characteristic physicochemical properties and biological activities, their degree of utility in organic synthesis depends largely on each element. For example, many organometallic complexes of titanium, zirconium, chromium, manganese, and the lanthanides play important roles as reagents or catalysts in organic synthesis, whereas technetium and actinide complexes are rarely used in synthesis despite their unique reactivity. It is also true that the well-characterized complexes prepared by reliable methods are not always important in synthesis because of their relatively lower reactivity, and, in contrast, in some cases, the uncharacterized reactive complexes are very useful for organic transformations. The main aim of Science of Synthesis is to provide useful methods for the synthesis of target compounds with descriptions of their scientific aspects rather than to describe all types of complexes comprehensively. Describing a variety of organometallic complexes of the early transition metals in a systematic manner according to the concept of Science of Synthesis does not constitute an easy task. Therefore, some chapters in this volume deal mostly with complexes that are not always synthetically useful but structurally interesting and/or important in other scientific fields.

In general, each chapter consists of a product class of one element, whereas chromium, molybdenum, and tungsten are described in a combined product class to avoid the redundancy of the closely related methods. A similar approach is also employed for niobium and tantalum, zirconium and hafnium, and for scandium, yttrium, and the lanthanides. Each product class is divided into product subclasses that are described in order of descending hapticity of the ligands. The section Applications [of the Product Subclass] in Organic Synthesis is utilized when the product subclass is employed as a reagent or catalyst in organic transformations. Synthetically important but uncharacterized complexes are also described in this section.

An unexpectedly long time has passed since this project started. The delay in publication is due to some changes in the guidelines for authors and my lack of experience in this type of editorial work. In this regard, I deeply apologize to the authors who submitted their manuscripts a considerably long time ago.

It is my great pleasure to thank Professor Ryoji Noyori and Dr. Guido F. Herrmann for their helpful discussions on the overview of this volume. I am very grateful to all the authors for their active participation in the development of our common project. Appreciation is also due to their cooperation to accept suggestions and comments that were given by the editorial office and me.

I am deeply indebted to the Science of Synthesis team of the publishing house, especially Dr. M. Fiona Shortt, Dr. Karen M. Muirhead, and Ms. Lindsey A. Sturdy for their enthusiastic cooperation to complete this project.

Chiba, April 2002

Volume Editor

Tsuneo Imamoto

Volume 2: Compounds of Groups 7–3 (Mn⋯, Cr⋯, V⋯, Ti⋯, Sc⋯, La⋯, Ac⋯)

Preface

Volume Editor’s Preface

Table of Contents

Introduction

T. Imamoto

2.1 Product Class 1: Organometallic Complexes of Manganese

K. Oshima

2.2 Product Class 2: Organometallic Complexes of Technetium

I. D. Gridnev and T. Imamoto

2.3 Product Class 3: Organometallic Complexes of Rhenium

F. E. Kühn, C. C. Romao, and W. A. Herrmann

2.4 Product Class 4: Arene Organometallic Complexes of Chromium, Molybdenum, and Tungsten

E. P. Kundig and S. H. Pache

2.5 Product Class 5: Organometallic π-Complexes of Chromium, Molybdenum, and Tungsten Excluding Arenes

K. H. Theopold, A. Mommertz, and B. A. Salisbury

2.6 Product Class 6: Organometallic Complexes of Chromium, Molybdenum, and Tungsten without Carbonyl Ligands

R. Poli and K. M. Smith

2.7 Product Class 7: Carbonyl Complexes of Chromium, Molybdenum, and Tungsten with σ-Bonded Ligands

T. Ito and M. Minato

2.8 Product Class 8: Organometallic Complexes of Vanadium

T. Imamoto and I. D. Gridnev

2.9 Product Class 9: Organometallic Complexes of Niobium and Tantalum

K. Mashima and A. Nakamura

2.10 Product Class 10: Organometallic Complexes of Titanium

K. Mikami, Y. Matsumoto, and T. Shiono

2.11 Product Class 11: Organometallic Complexes of Zirconium and Hafnium

E. -i. Negishi and T. Takahashi

2.12 Product Class 12: Organometallic Complexes of Scandium, Yttrium and the Lanthanides

Z. Hou and Y. Wakatsuki

2.13 Product Class 13: Organometallic Complexes of the Actinides

A. Dormond and D. Barbier-Baudry

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!