The Chemistry of Organic Derivatives of Gold and Silver Edited by Saul Patai and Zvi Rappoport Copyright  1999 John Wiley & Sons, Ltd ISBN: 0-471-98164-8 The chemistry of organic derivatives of gold and silver THE CHEMISTRY OF FUNCTIONAL GROUPS A series of advanced treatises under the general editorship of Professors Saul Patai and Zvi Rappoport The chemistry of alkenes (2 volumes) The chemistry of the carbonyl group (2 volumes) The chemistry of the ether linkage The chemistry of the amino group The chemistry of the nitro and nitroso groups (2 parts) The chemistry of carboxylic acids and esters The chemistry of the carbon – nitrogen double bond The chemistry of amides The chemistry of the cyano group The chemistry of the hydroxyl group (2 parts) The chemistry of the azido group The chemistry of acyl halides The chemistry of the carbon – halogen bond (2 parts) The chemistry of the quinonoid compounds (2 volumes, parts) The chemistry of the thiol group (2 parts) The chemistry of the hydrazo, azo and azoxy groups (2 volumes, parts) The chemistry of amidines and imidates (2 volumes) The chemistry of cyanates and their thio derivatives (2 parts) The chemistry of diazonium and diazo groups (2 parts) The chemistry of the carbon – carbon triple bond (2 parts) The chemistry of ketenes, allenes and related compounds (2 parts) The chemistry of the sulphonium group (2 parts) Supplement A: The chemistry of double-bonded functional groups (3 volumes, parts) Supplement B: The chemistry of acid derivatives (2 volumes, parts) Supplement C: The chemistry of triple-bonded functional groups (2 volumes, parts) Supplement D: The chemistry of halides, pseudo-halides and azides (2 volumes, parts) Supplement E: The chemistry of ethers, crown ethers, hydroxyl groups and their sulphur analogues (2 volumes, parts) Supplement F: The chemistry of amino, nitroso and nitro compounds and their derivatives (2 volumes, parts) The chemistry of the metal – carbon bond (5 volumes) The chemistry of peroxides The chemistry of organic selenium and tellurium compounds (2 volumes) The chemistry of the cyclopropyl group (2 volumes, parts) The chemistry of sulphones and sulphoxides The chemistry of organic silicon compounds (2 volumes, parts) The chemistry of enones (2 parts) The chemistry of sulphinic acids, esters and their derivatives The chemistry of sulphenic acids and their derivatives The chemistry of enols The chemistry of organophosphorus compounds (4 volumes) The chemistry of sulphonic acids, esters and their derivatives The chemistry of alkanes and cycloalkanes Supplement S: The chemistry of sulphur-containing functional groups The chemistry of organic arsenic, antimony and bismuth compounds The chemistry of enamines (2 parts) The chemistry of organic germanium, tin and lead compounds The chemistry of dienes and polyenes The chemistry of organic derivatives of gold and silver UPDATES The chemistry of ˛-haloketones, ˛-haloaldehydes and ˛-haloimines Nitrones, nitronates and nitroxides Crown ethers and analogs Cyclopropane derived reactive intermediates Synthesis of carboxylic acids, esters and their derivatives The silicon – heteroatom bond Synthesis of lactones and lactams Syntheses of sulphones, sulphoxides and cyclic sulphides Patai’s 1992 guide to the chemistry of functional groups — Saul Patai C Au C Ag The chemistry of organic derivatives of gold and silver Edited by SAUL PATAI and ZVI RAPPOPORT The Hebrew University, Jerusalem 1999 JOHN WILEY & SONS, LTD CHICHESTER – NEW YORK – WEINHEIM – BRISBANE – SINGAPORE – TORONTO An Interscience Publication Copyright  1999 John Wiley & Sons Ltd, Baffins Lane, Chichester, West Sussex PO19 1UD, England National 01243 779777 International (C44) 1243 779777 e-mail (for orders and customer service enquiries): cs-books@wiley.co.uk Visit our Home Page on http://www.wiley.co.uk or http://www.wiley.com All Rights Reserved No part of this publication may be reproduced, stored in a retrieval system, or transmitted, in any form or by any means, electronic, mechanical, photocopying, recording, scanning or otherwise, except under the terms of the Copyright Designs and Patents Act 1988 or under the terms of a licence issued by the Copyright Licensing Agency, 90 Tottenham Court Road, London W1P 9HE, UK, without the permission in writing of the Publisher Other Wiley Editorial Offices John Wiley & Sons, Inc., 605 Third Avenue, New York, NY 10158-0012, USA WILEY-VCH Verlag GmbH, Pappelallee 3, D-69469 Weinheim, Germany Jacaranda Wiley Ltd, 33 Park Road, Milton, Queensland 4064, Australia John Wiley & Sons (Asia) Pte Ltd, Clementi Loop #02-01, Jin Xing Distripark, Singapore 129809 John Wiley & Sons (Canada) Ltd, 22 Worcester Road, Rexdale, Ontario M9W 1L1, Canada Library of Congress Cataloging-in-Publication Data The chemistry of organic derivatives of gold and silver / edited by Saul Patai and Zvi Rappoport p cm — (The chemistry of functional groups) ‘An Interscience publication.’ Includes bibliographical references and index ISBN 0-471-98164-8 (alk paper) Organogold compounds Organosilver compounds I Patai, Saul II Rappoport, Zvi III Series QD412.A9C48 1999 98-14487 5470 0565 — dc21 British Library Cataloguing in Publication Data A catalogue record for this book is available from the British Library ISBN 471 98164 Typeset in 9/10pt Times by Laser Words, Madras, India Printed and bound in Great Britain by Biddles Ltd, Guildford, Surrey This book is printed on acid-free paper responsibly manufactured from sustainable forestry, in which at least two trees are planted for each one used for paper production To Lisl Patai How much better is it to get wisdom than gold! and to get understanding rather to be chosen than silver! Proverbs 16 : 16 Contributing authors R Alan Aitken School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife, KY16 9ST, Scotland, UK Harold Basch Department of Chemistry, Bar-Ilan University, Ramat-Gan 52900, Israel Angela Bayler Lehrstuhl făur Anorganische und Analytische Chemie, Technische Universităat Măunchen, D-85747 Garching, Germany Alice E Bruce Department of Chemistry, University of Maine, 5706 Aubert Hall, Orono, Maine 04469-5706, USA Mitchell R M Bruce Department of Chemistry, University of Maine, 5706 Aubert Hall, Orono, Maine 04469-5706, USA Victor Chechik Department of Chemistry, University of Sheffield, Dainton Building, Sheffield, S3 7HF, UK John P Fackler, Jr Department of Chemistry, Texas A & M University, College Station, Texas 77843-3012, USA Simon P Fricker AnorMED, Inc., 100 20353-64th Avenue, Langley, British Columbia, V2Y 1N5, Canada Sarina Grinberg Institutes for Applied Research, Ben-Gurion University of the Negev, Ernst David Bergman Campus, P O B 653, Beer-Sheeva 84110, Israel Andreas Grohmann Lehrstuhl făur Anorganische und Analytische Chemie, Technische Universităat Măunchen, D-85747 Garching, Germany William M Horspool Department of Chemistry, University of Dundee, Dundee, DD1 4HN, Scotland, UK Tova Hoz Department of Chemistry, Bar-Ilan University, Ramat-Gan 52900, Israel ´ Marianna Kanska Department of Chemistry, University of Warsaw, Warsaw, Poland ´ Ryszard Kanski Department of Chemistry, University of Warsaw, Warsaw, Poland ă Thomas M Klapotke Institut făur Anorganische Chemie, Universităat Măunchen (LMU), Butenandtstr 13 (Haus D), D-81377 Măunchen, Germany vii viii Contributing authors Joel F Liebman Department of Chemistry and Biochemistry, University of Maryland, Baltimore County Campus, 1000 Hilltop Circle, Baltimore, Maryland 21250, USA Ahmed A Mohamed Department of Chemistry, University of Maine, 5706 Aubert Hall, Orono, Maine 04469-5706, USA Igor Novak Department of Chemistry, National University of Singapore, Kent Ridge, Singapore 119260 M Elena Olmos Lehrstuhl făur Anorganische und Analytische Chemie, Technische Universităat Măunchen, D-85747 Garching, Germany R V Parish Department of Chemistry, UMIST, P.O Box 88, Manchester, M60 1QD, UK Annette Schier Lehrstuhl făur Anorganische und Analytische Chemie, Technische Universităat Măunchen, D-85747 Garching, Germany Hubert Schmidbaur Lehrstuhl făur Anorganische und Analytische Chemie, Technische Universităat Măunchen, D-85747 Garching, Germany C Frank Shaw III Department of Chemistry, University of Wisconsin at Milwaukee, P.O Box 413, Milwaukee, Wisconsin 53201-0413, USA ˜ Jose´ Martinho Simoes Departamento de Qu´ımica e Bioqu´ımica and CiTecMat, Faculdade de Ciˆencias, Universidade de Lisboa, 1700 Lisboa, Portugal Suzanne W Slayden Department of Chemistry, George Mason University, 4400 University Drive, Fairfax, Virginia 22030-4444, USA Charles J M Stirling Department of Chemistry, University of Sheffield, Dainton Building, Sheffield, S3 7HF, UK Suning Wang Department of Chemistry, Queen’s University, Kingston, Ontario K7L 3N6, Canada Jacob Zabicky Institutes for Applied Research, Ben-Gurion University of the Negev, Ernst David Bergman Campus, P O B 653, Beer-Sheeva 84110, Israel ´ Mieczysław Zielinski Isotope Laboratory, Faculty of Chemistry, Jagiellonian University, ul Ingardena 3, 30-060 Krakow, Poland Foreword In recent years The Chemistry of Functional Groups has included several volumes dealing with the chemistry of organometallic derivatives (five volumes edited by F Hartley in 1982 –1989), and The chemistry of organic germanium, tin and lead compounds (Ed S Patai, 1995) For the reason outlined below, this volume deals with the chemistry of organosilver and organogold compounds The volume contains 16 chapters dealing with calculations on organogold compounds, physical and spectroscopic properties (NMR, ESR, PES, Măossbauer spectra), thermochemical and analytical properties, the synthesis and uses of the title compounds and their reactions such as rearrangements, pyrolysis and photochemical reactions The medicinal use of organogold compounds and the increased use of gold –thiol monolayers are also summarized The literature coverage is mostly up to 1998 I would be grateful to readers who call my attention to mistakes in the present volume ZVI RAPPOPORT Jerusalem February, 1999 ix Photo: Schwerin/Bernheim SAUL PATAI 1918–1998 ... parts) The chemistry of enones (2 parts) The chemistry of sulphinic acids, esters and their derivatives The chemistry of sulphenic acids and their derivatives The chemistry of enols The chemistry of. .. esters The chemistry of the carbon – nitrogen double bond The chemistry of amides The chemistry of the cyano group The chemistry of the hydroxyl group (2 parts) The chemistry of the azido group The. .. of the carbonyl group (2 volumes) The chemistry of the ether linkage The chemistry of the amino group The chemistry of the nitro and nitroso groups (2 parts) The chemistry of carboxylic acids and