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Advances-In-Inorganic-Chemistry-50 Advances in INORGANIC CHEMISTRY Volume 50 ADVISORY BOARD I. Bertini J. Reedijk Universita´ degli Studi di Firenze Leiden University Florence, Italy Leiden, The Netherlands A. H. Cowley P. J. Sadler University of Edinburgh University of Texas Edinburgh, Scotland Austin, Texas, USA A. M. Sargeson H. B. Gray The Australian National University California Institute of Technology Canberrs, Australia Pasadena, California, USA Y. Sasaki M. L. H. Green Hokkaido University University of Oxford Sapporo, Japan Oxford, United Kingdom D. F. Shriver O. Kahn Northwestern University Evanston, Illinois, USA Institut de Chimie de la Matie`re Condense´e de Bordeaux Pessac, France R. van Eldik Universita¨t Erlangen-Nu¨mberg Andre´E. Merbach Erlangen, Germany Institut de Chimie Mine ´rale et Analytique K. Wieghardt Universite´ de Lausanne Max-Planck Institut Lausanne, Switzerland Mu¨lheim, Germany Advances in INORGANIC CHEMISTRY Main Group Chemistry EDITED BY A. G. Sykes Department of Chemistry The University of Newcastle Newcastle upon Tyne United Kingdom CO-EDITED BY Alan H. Cowley Department of Chemistry and Biochemistry The University of Texas at Austin Austin, Texas VOLUME 50 San Diego San Francisco New York Boston London Sydney Tokyo This book is printed on acid-free paper. ᭺ȍ Copyright 2000 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. 0898-8838/00 $35.00 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 NW1 7DX, UK http://www.hbuk.co.uk/ap/ International Standard Book Number: 0-12-023650-8 PRINTED IN THE UNITED STATES OF AMERICA 000102030405QW987654321 CONTENTS The Reactions of Stable Nucleophilic Carbenes with Main Group Compounds CLAIRE J. CARMALT AND ALAN H. COWLEY I. Introduction .........1 II. Group 1, 2, and 12 Complexes ......3 III. Group 13 Complexes ........9 IV. Silicon, Germanium, Tin, and Lead Complexes ....16 V. Group 15 Complexes ........20 VI. Sulfur, Selenium, and Tellurium Complexes ....22 VII. Halogen Complexes ........25 VIII. Conclusions .........28 References .........29 Group I Complexes of P- and As-Donor Ligands KEITH IZOD I. Introduction .........33 II. Charge-Localized Ligands .......35 III. Charge-Delocalized Ligands .......70 IV. Tertiary Phosphine-Functionalized Ligands .....89 V. Miscellaneous Complexes .......97 VI. Conclusion .........101 References .........101 Aqueous Solution Chemistry of Beryllium LUCIA ALDERIGHI,PETER GANS,STEFANO MIDOLLINI, AND ALBERTO VACCA I. Introduction .........109 II. Properties of Beryllium ........115 III. The Beryllium Ion ........115 IV. Beryllium Hydrolysis ........116 V. Interaction with Inorganic Ligands ......131 VI. Interaction with Organic Ligands ......136 VII. Conclusions .........163 References .........164 v vi CONTENTS Group 2 Element Precursors for the Chemical Vapor Deposition of Electronic Materials JASON S. MATTHEWS AND WILLIAM S. REES JR. Text ...........173 References ..........190 Molecular, Complex Ionic, and Solid-State PON Compounds ROGER MARCHAND,WOLFGANG SCHNICK, AND NORBERT STOCK I. Introduction .........193 II. Molecular PON Compounds .......194 III. Acyclic Molecular Ionic PON Compounds .....195 IV. Cyclic PON Compounds ........197 V. Solid-State PON Compounds .......209 VI. Conclusion .........225 References .........226 Molecular Clusters of Dimetalated Primary Phosphanes and Arsanes MATTHIAS DRIESS I. Introduction .........236 II. Dilithiation and Disodiation of Primary Phosphanes and Arsanes . 241 III. Dicopper Phosphandiides .......258 IV. Magnesium Phosphandiides .......259 V. Tin(II) Phosphandiides........262 VI. Aluminum, Gallium, and Indium Phosphandiides and Arsandiides . 267 VII. Mixed-Metalated Phosphandiides and Arsandiides ....274 VIII. Conclusion .........280 References .........282 Coordination Complexes of Bismuth(III) Involving Organic Ligands with Pnictogen or Chalcogen Donors GLEN G. BRIAND AND NEIL BURFORD I. Introduction and Scope .......286 II. Alkoxides, Thiolates, and Selenolates .....290 III. Carboxylates, Thiocarboxylates, Dithiocarboxylates, and Diselenocarboxylates .......300 IV. Ethers and Thioethers ........309 V. Ketones and Thiones ........315 VI. Amides ..........318 CONTENTS vii VII. Amines, Phosphines, and Arsines ......320 VIII. Nonsymmetric Bifunctional and Multifunctional Ligands . 328 IX. Conclusions .........349 References .........349 Phanes Bridged by Group 14 Heavy Elements HIDEKI SAKURAI I. Introduction .........359 II. An Introductory Case Study on 3,4,7,8-Tetrasilacycloocta-1,5-diyne . 361 III. [2.2]Cyclophanes ........363 IV. Tetrasila[2.2](2,5)heterophanes ......380 V. Hexasila[2.2.2](1,3,5)cyclophane ......391 VI. [2n]Paracyclophanes Bridged by Si, Ge, and Sn ....395 VII. [n]Cyclophanes Bridged by Si .......400 VIII. Conclusion .........405 References .........406 INDEX ..........409 CONTENTS OF PREVIOUS VOLUMES ......421 ThisPageIntentionallyLeftBlank ADVANCES IN INORGANIC CHEMISTRY, VOL. 50 THE REACTIONS OF STABLE NUCLEOPHILIC CARBENES WITH MAIN GROUP COMPOUNDS CLAIRE J. CARMALT* and ALAN H. COWLEY† *Department of Chemistry, University College London, Christopher Ingold Laboratories, London, WC1H 0AJ, United Kingdom and †Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin, Texas, 78712 I. Introduction II. Group 1, 2, and 12 Complexes A. Alkali Metals and Hydrogen B. Alkaline Earth Metals, Zinc, and Mercury III. Group 13 Complexes A. Group 13 Trihalides B. Group 13 Trihydrides C. Group 13 Trialkyls and Triaryls IV. Silicon, Germanium, Tin, and Lead Complexes A. Silicon Halides and Organosilicon Compounds B. Germanium and Tin Halides and Organotin Halides C. Cyclopropenylidene Complexes of Divalent Germanium, Tin, and Lead Amides V. Group 15 Complexes A. Phosphinidenes and Arsnidenes B. Phosphoranes VI. Sulfur, Selenium, and Tellurium Complexes VII. Halogen Complexes VIII. Conclusions References I. Introduction Carbenes play important roles both as reactive intermediates and also as ligands; consequently, considerable effort has been devoted to understanding their molecular and electronic structures. Special interest is associated with carbenes that feature the attachment of donor groups to the carbenic carbon since they behave as nucleophiles and, in some instances, can be isolated. Pioneering work on nucleo- 1 Copyright 2000 by Academic Press. All rights of reproduction in any form reserved. 0898-8838/00 $35.00 2 CARMALT AND COWLEY philic carbenes was carried out by Wanzlick and co-workers (1), who, in the early 1960s, examined the reactivity patterns of species such as 1 (R ϭ Ph) that were generated in situ by C-deprotonation of the Ϫ t precursor, 2 (R ϭ Ph, X ϭ ClO4 ), with KO Bu. Although 1 bears an obvious relationship to the electron-rich olefin, 3, the latter is not in equilibrium with the corresponding carbene. Wanzlick et al. also pre- dicted that carbene 4 (RЈϭR ϭ Ph) would possess enhanced stability due to the possibility of aromatic resonance and demonstrated the intermediacy of this species by C-deprotonation of imidazolium salt 5 Ϫ Ϫ t (RЈϭR ϭ Ph; X ϭ ClO4 ) with KO Bu, followed by trapping with phenylisothiocyanate (2) or mercuric chloride (3)(vide infra). How- ever, several years were to elapse before Arduengo et al. (4) achieved the first isolation of a stable, crystalline nucleophilic carbene, 4 (RЈϭH; R ϭ adamantyl) by C-deprotonation of the corresponding bis(1-adamantyl)imidazolium chloride with KH. This important de- velopment prompted a flurry of activity in this area of chemistry. For example, a completely new synthetic route to stable nucleophilic car- benes has been developed by Kuhn et al. (5), viz. the reduction of thiones with potassium in THF, and Herrmann et al. (6) demon- strated that a liquid ammonia/THF solvent system is very effective for the NaH deprotonation of imidazolium salts at relatively low tem- peratures. The range of stable nucleophilic carbenes has also ex- panded significantly, not only in terms of the elaboration of substitu- REACTIONS OF NUCLEOPHILIC CARBENES WITH MAIN GROUP COMPOUNDS 3 ents on structures of type 4, but also from the standpoint of new structural types (7). The isolation of saturated derivatives of types 1 (R ϭ Mes) (8) and 6 (R ϭ iPr) (9) implies that the presence of a car- bon–carbon double bond is not, in fact, a prerequisite for stability. Moreover, Alder et al. (10) have shown that, with the appropriate sub- stituents,
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