E-Book Content
Advances in
ORGANOMETALLIC CHEMISTRY VOLUME 20
CONTRIBUTORS TO THIS VOLUME Gordon K. Anderson
F.
E. Brinckman
R. J. P. Corriu J. A. Gladysz C. Guerin Wolfgang A. Herrmann John S. Thayer Shen Yanchang (Y. C. Shen) Huang Yaozeng (Y. 2 . Huang)
Advances in Orga n ometallic Chemis try EDITED BY
F. G. A. STONE
ROBERT WEST
DEPARTMENT OF INORGANIC CHEMISTRY
DEPARTMENT O F CHEMISTRY UNIVERSITY OF WISCONSIN
UNIVERSITY OF BRISTOL
MADISON WISCONSIN
BRISTOL. ENGLAND
VOLUME 20
1982 ACADEMIC PRESS A Subsidiary of Harcourt Brace Jovanovich. Publishers
New York London Paris San Diego San Francisco Sao Paulo Sydney Tokyo Toronto
COPYRIGHT @ 1982, BY ACADEMIC PRESS, INC. ALL RIGHTS RESERVED. NO PART O F THIS PUBLICATION MAY BE REPRODUCED OR TRANSMITTED IN ANY FORM OK BY ANY MEANS, ELECTRONIC OR MECHANICAL, INCLUDING PHOTOCOPY, RECORDING, OR ANY INFORMATION STORAGE AND RETRIEVAL SYSTEM, WITHOUT PERMISSION IN WRITING FROM T H E PUBLISHER.
ACADEMIC PRESS, INC.
11 1 Fifth Avenue, N e w York, New York 10003
United Kirlgdotn Edifiou prrblished by ACADEMIC PRESS, INC. ( L O N D O N ) LTD. 24/28 Oval Road, Lo n do n N W 1 7DX
LIBRARY OF
CONGRESS CATALOG CARD
NUMBER: 64- 16030
ISBN 0-1 2-031 120 -8 PRINTED IN THE UNITED STATES OF AMERICA
82 83 84 85
9 8 7 6 5 4 3 2 1
Contents ix
L I ~ OTF C O\ T KI HU T O R S
Transition Metal Formyl Complexes
J . A . GLADYSZ I. 11. 111. IV. V. VI.
I 3
Introduction Synthesis of Transition Metal Formyl Complexes Physical Properties of Tramition Metal Formyl Complexes Reactions of Transition Metal F'ormyl Complexes ropics Relating to the Stability and Decomposition ot Trmsition Metal Formyl Complexes Conclusion Addendum References
13
15
26 33 34
35
The Organic Chemistry of Gold
GORDON K. ANDERSON I.
Introduction
40 41
11. Organogold(1) Complexes Preparation dnd ChdrdCterlZdtiOn
Reactions of Organogold(1) Complexe\ Organogold(II1) Complexes Preparation and Characterization Reactions of Organogold(II1) Complexes Compansons of Bonding, Spectra, and Reactivity ot Organogold( I ) and Organogold(II1) Complexe\ VII. Compansons of Organogold Complexe5 with Thobe of Other Metal4 References
63
111. I v. V. VI.
I2 89 94 101 I05
Arsonium Ylides
HUANG YAOZENG (Y. Z. HUANG) and SHEN YANCHANG (Y. C . S H E N ) I. 11. 111. IV.
Introduction . . . . . . . . . . Methods of Preparation . . . . . . . . . . . . . Structure and Physical Properties . . . . . . . . . Chemical Reactions and Synthetic Applications . . . V
.
.
.
.
.
.
. . . . . . . . . . . . . .
.
.
115 116
I25 134
vi
Contents
V. Conclusion References
. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
153 155
The Methylene Bridge
WOLFGANG A . HERRMANN I . Introduction . . . . . . . . . . . . . . . . . . . . . . . . I1 . Nomenclature . . . . . . . . . . . . . . . . . . . . . . . . 111. Historical Background . . . . . . . . . . . . . . . . . . . . . . I v. Synthesis of p-Methylene Transition Metal Complexes . . . . . . . . V. Theory and Bonding in Simple Dimetallacyclopropane Complexes . . . VI . Structural Features of p-Methylene Metal Complexes . . . . . . . . VII . Spectroscopic Characterization of p-Methylene Metal Complexes . . . VIII . Reactivity of Methylene-Bridged Transition Metal Complexes . . . . . IX . Catalytic Implications of the Methylene Bridge . . .