Advances in Organometallic Chemistry
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Advances in ORGANOMETALLJC CHEMISTRY VOLUME 43 This Page Intentionally Left Blank Advances in Organometallic Chemistry EDITED BY ROBERT WEST ANTHONY F. HILL DEPARTMENT OF CHEMISTRY DEPARTMENT OF CHEMISTRY UNIVERSITY OF WISCONSIN IMPERIAL COLLEGE OF SCIENCE, MADISON, WISCONSIN TECHNOLOGY, AND MEDICINE LONDON, ENGLAND FOUNDING EDITOR F. GORDON A. STONE VOLUME 43 ACADEMIC PRESS San Diego London Boston New York Sydney Tokyo Toronto This book is printed on acid-free paper. @ Copyright 0 1999 by ACADEMIC PRESS All Rights Reserved. No part of this publication may be reproduced or transmitted in any form or by any means, electronic or mechanical, including photocopy, recording, or any information storage and retrieval system, without permission in writing from the Publisher. The appearance of the code at the bottom of the first page of a chapter in this book indicates the Publisher’s consent that copies of the chapter may be made for personal or internal use of specific clients. This consent is given on the condition, however, that the copier pay the stated per copy fee through the Copyright Clearance Center, Inc. (222 Rosewood Drive, Danvers, Massachusetts 01923). for copying beyond that permitted by Sections 107 or 108 of the U.S. Copyright Law. This consent does not extend to other kinds of copying, such as copying for general distribution, for advertising or promotional purposes, for creating new collective works, or for resale. Copy fees for pre-1998 chapters are as shown on the title pages. If no fee code appears on the title page, the copy fee is the same as for current chapters. 0065-3055/99 $25.00 Academic Press a division of Harcourt Brace & Company 525 B Street, Suite 1900, San Diego, California 92101-4495, USA http://www.apnet.com Academic Press Limited 24-28 Oval Road, London NW 1 7DX, UK http:/lwww.hbuk.co.uk/ap/ International Standard Book Number: 0-12-031 143-7 PRINTED IN THE UNlTED STATES OF AMERICA 98 99 0001 02 03QW 9 8 7 6 5 4 321 Contents CONTRIBUTORS.. ix PREFACE... xi Silylenes Coordinated to Lewis Bases JOHANNES BELZNER and HEIKO IHMELS I. Introduction . 1 11. Theoretical Studies of Silylene-Lewis Base Complexes . 2 111. Spectroscopic Properties of Silylene-Lewis Base Adducts . , . 11 IV. Kinetic Studies . 16 V. Donor-Acceptor Interactions of Silylenes in Organometallic Reactions . 19 References. 40 Chemistry of Ruthenium-Carbide Clusters RU,C(CO),~ and Ru,C(CO),, PAUL J. DYSON I. Introduction . 44 11. Synthesis and Characterization of RU~C(CO)~~and Ru&(C0)17 . 44 111. Electrochemistry. 48 EV . Ligand Reactions of RLI~C(CO)~~and RU~C(CO)~~.. 49 V. Derivatives of RU~C(CO)~~and RU~C(CO)~, Prepared from Other Clusters 88 VI. Origin of the Carbide Atom in RU~C(CO)~,and Some of Its Derivatives . 96 VII. Reactions of Ru~C(CO)~~and RU~C(CO)~~ That Result in Higher Nuclearity Clusters . 99 VIII. Heteronuclear Derivatives . 103 IX. Stereochemical Nonrigid Behavior . 116 X. Concluding Remarks . , . 118 References. 119 V VI Contents Transition Metal Heteroaldehyde and Heteroketone Complexes HELMUT FISCHER. RUDIGER STUMPF. and GERHARD ROTH I . Introduction ....................... 125 I1. Bonding in Heteroaldehydes and Heteroketones .......... 127 111. Bonding and Structure in Heteroaldehyde and Heteroketone Complexes . 128 IV . Synthesis of Heteroaldehyde and Heteroketone Complexes ....... 140 V . Reactions of Heteroaldehyde and Heteroketone Complexes ...... 173 References ........................ 189 Recent Progress in Transition Metal-Catalyzed Reactions of Silicon. Germanium. and Tin JENNIFER A . REICHL and DONALD H . BERRY I . Introduction ....................... 197 I1 . Formation of E-C Bonds .................. 199 IT1. Formation of E-E Bonds .................. 243 IV. Formation of Si-0 Bonds .................. 248 V . Formation of Si-N Bonds .................. 254 VI . Conclusions ....................... 257 References ........................ 258 Organometallic Compounds of the Heavier Alkali Metals J . DAVID SMITH I . Introduction ....................... 267 11 . Synthesis ........................ 269 IT1 . Alkyl Derivatives ..................... 271 IV. Aryl Derivatives ...................... 292 V . Cyclopentadienyl and Related Derivatives ............ 294 VI . Alkene and Alkyne Derivatives ................ 309 VII . Arene Derivatives ..................... 326 VIII . Conclusions ....................... 342 References ........................ 343 Organometallic Complexes in Nonlinear Optics II: Third-Order Nonlinearities and Optical Limiting Studies IAN R . WHITTALL. ANDREW M . McDONAGH. MARK G . HUMPHREY. and MAREK SAMOC 1 . Introduction ....................... 349 I1. Background ....................... 352 Contents vii 111. Organometallics for Third-Order Nonlinear Optics ....... 368 IV . Optical Limiting Properties of Organometallic Complexes .... 398 V . Concluding Remarks ................. 401 VI . Appendix: Abbreviations ................ 401 References ..................... 402 INDEX ..................... 401 CUMULATIVELIST OF CONTRIBUTORSFOR VOLUMES 1-36 .... 419 CUMULATIVEINDEX FOR VOLUMES31-43 ......... 423 This Page Intentionally Left Blank Contributors Numbers in parentheses indicate the pages on which the authors' contributions begiri JOHANNES BELZNER (l), Institut fur Organische Chemie der Georg-August-Universitat Gottingen, D-37077 Gottingen, Germany DONALD H. BERRY (197), Department of Chemistry and Laboratory for Research on the Structure of Matter, University of Pennsylvania, Philadelphia, Pennsylvania 19104 PAUL J. DYSON (43), Centre for Chemical Synthesis, Department of Chemistry, Imperial College of Science, Technology, and Medicine, South Kensington, London SW7 2AY, United Kingdom HELMUT FISCHER (125), Fakultat fur Chemie, Universitat Konstanz, Fach M727, D-78457 Konstanz, Germany MARK G. HUMPHREY (349), Department of Chemistry, Australian National University, Canberra, ACT 0200, Australia HEIKO IHMELS (l),Institut fur Organische Chemie der Universitat Wurzburg, D-97074 Wiirzburg, Germany ANDREW M. MCDONAGH (349), Department of Chemistry, Australian National Univer- sity, Canberra, ACT 0200, Australia JENNIFER A. REICHL, Department of Chemistry and Laboratory for Research on the Structure of Matter, University of Pennsylvania, Philadelphia, Pennsylvania 19104 GERHARD ROTH (125), Fakultat fur Chemie, Universitat Konstanz, Fach M727, D-78457 Konstanz, Germany MAREK SAMOC (349), Australian Photonics Cooperative Research Centre, Laser Physics Centre, Research School of Physical Sciences and Engineering, Australian National Univer- sity, Canberra, ACT 0200, Australia J. DAVID SMITH (267), School of Chemistry, Physics, and Environmental Science, University of Sussex, Brighton BN1 9QJ, United Kingdom RUDIGER STUMPF (129, Fakultat fur Chemie, Universitat Konstanz, Fach M727, D-78457 Konstanz, Germany IAN R. WHITTALL (349), Department of Chemistry, Australian National University, Can- berra, ACT 0200, Australia ix This Page Intentionally Left Blank Preface This 43rd volume of Advances in Orgunometullic Chemistry marks the transition of Professor F. Gordon A. Stone, F.R.S., C.B.E., to the status of Founding Editor of the series that he instigated and coedited for 34 years. Organometallic chemistry has grown dramatically over the past four decades. Research in this vibrant field is by nature dendritic; each year has brought new divergences and subdisciplines. It is therefore easy to forget how nascent the field was when this series began in 1964, prefaced by the words: “Organometallic chemistry now seems well on its way toward establishing its identity as an important domain of science . We hope that chemists with a general interest in this field will, turning these pages, be able to find recent information about many of the most active areas in organometallic chemistry.” In the interim, Gordon’s breadth of interest and insight has allowed him to identify emergent fields and rising scientists. Forty-three volumes later, over 350 invited authors have contributed to this goal of providing an author list that reads like an organometallic chemist’s “Who’s Who.” The enormous impact of Gordon Stone’s research in organometallic chemistry continues to receive wide recognition. His long list of honorary doctorates, prestigious awards and commendations, and visiting pro- fessorships and the establishment of the “Gordon Stone Lectures” attest to the central role he has played in the development of our science. Moreover, he has been a champion of the support of fundamental research through his considerable influence on science policy on both sides of the Atlantic. On this occasion, it is particularly appropriate to consider Gordon’s contributions to scholarship and scientific publishing. He has served in an editorial or advisory role to every key journal concerned with our science. With E. W. Abel and G. Wilkinson, he conceived of and coedited the preeminent and essential reference works in our field, Comprehensive Organometallic Chemistry, editions 1 and 2. We are pleased to congratulate Gordon on these achievements and to welcome him in his new role as Founding Editor. His continued advice and enthusiasm for the series will be invaluable. We both wish him all the best in his continuing researches. Robert West Anthony F. Hill xi This Page Intentionally Left Blank ADVANCES IN ORGANOMETALLIC CHEMISTRY, VOL. 43 Siylenes Coordinated to Lewis Bases JOHANNES BELZNER lnstitut fiir Organische Chemie der Georg-August-Universiiat Gottingen 0-37077 Gottingen, Germany HEIKO IHMELS lnstitut fiir Organische Chernie der