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The Chemistry of Organic Silicon Compounds, Volume 3 PDF

2780 Pages·2001·21.805 MB·English
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Preview The Chemistry of Organic Silicon Compounds, Volume 3

The chemistry of organic silicon compounds Volume 2 THECHEMISTRY OFFUNCTIONALGROUPS Aseriesofadvancedtreatisesunderthegeneraleditorshipof ProfessorsSaulPataiandZviRappoport Thechemistryofalkenes(2volumes) Thechemistryofthecarbonylgroup(2volumes) Thechemistryoftheetherlinkage Thechemistryoftheaminogroup Thechemistryofthenitroandnitrosogroups(2parts) Thechemistryofcarboxylicacidsandesters Thechemistryofthecarbon nitrogendoublebond Thechemistryofamides Thechemistryofthecyanogroup Thechemistryofthehydroxylgroup(2parts) Thechemistryoftheazidogroup Thechemistryofacylhalides Thechemistryofthecarbon halogenbond(2parts) Thechemistryofthequinonoidcompounds(2volumes,4parts) Thechemistryofthethiolgroup(2parts) Thechemistryofthehydrazo,azoandazoxygroups(2volumes,3parts) Thechemistryofamidinesandimidates(2volumes) Thechemistryofcyanatesandtheirthioderivatives(2parts) Thechemistryofdiazoniumanddiazogroups(2parts) Thechemistryofthecarbon carbontriplebond(2parts) Thechemistryofketenes,allenesandrelatedcompounds(2parts) Thechemistryofthesulphoniumgroup(2parts) SupplementA:Thechemistryofdouble-bondedfunctionalgroups(3volumes,6parts) SupplementB:Thechemistryofacidderivatives(2volumes,4parts) SupplementC:Thechemistryoftriple-bondedfunctionalgroups(2volumes,3parts) SupplementD:Thechemistryofhalides,pseudo-halidesandazides(2volumes,4parts) SupplementE:Thechemistryofethers,crownethers,hydroxylgroups andtheirsulphuranalogues(2volumes,3parts) SupplementF:Thechemistryofamino,nitrosoandnitrocompoundsandtheirderivatives (2volumes,4parts) Thechemistryofthemetal carbonbond(5volumes) Thechemistryofperoxides Thechemistryoforganicseleniumandtelluriumcompounds(2volumes) Thechemistryofthecyclopropylgroup(2volumes,3parts) Thechemistryofsulphonesandsulphoxides Thechemistryoforganicsiliconcompounds(2volumes,5parts) Thechemistryofenones(2parts) Thechemistryofsulphinicacids,estersandtheirderivatives Thechemistryofsulphenicacidsandtheirderivatives Thechemistryofenols Thechemistryoforganophosphoruscompounds(4volumes) Thechemistryofsulphonicacids,estersandtheirderivatives Thechemistryofalkanesandcycloalkanes SupplementS:Thechemistryofsulphur-containingfunctionalgroups Thechemistryoforganicarsenic,antimonyandbismuthcompounds Thechemistryofenamines(2parts) Thechemistryoforganicgermanium,tinandleadcompounds UPDATES Thechemistryof˛-haloketones,˛-haloaldehydesand˛-haloimines Nitrones,nitronatesandnitroxides Crownethersandanalogs Cyclopropanederivedreactiveintermediates Synthesisofcarboxylicacids,estersandtheirderivatives Thesilicon heteroatombond Synthesisoflactonesandlactams Synthesesofsulphones,sulphoxidesandcyclicsulphides Patai’s1992guidetothechemistryoffunctionalgroups SaulPatai C Si Si X The chemistry of organic silicon compounds Volume 2 Edited by ZVI RAPPOPORT TheHebrewUniversity,Jerusalem and YITZHAK APELOIG Technion IsraelInstituteofTechnology,Haifa 1998 JOHN WILEY &SONS CHICHESTER NEWYORK WEINHEIM BRISBANE SINGAPORE TORONTO AnInterscience(cid:1)R Publication Copyright1998JohnWiley&SonsLtd, BaffinsLane,Chichester, WestSussexPO191UD,England National 01243779777 International(C44)1243779777 e-mail(forordersandcustomerserviceenquiries):[email protected] VisitourHomePageonhttp://www.wiley.co.uk orhttp://www.wiley.com All Rights Reserved. No part of this publication may be reproduced, stored in a retrieval system, or transmitted,inanyformorbyanymeans,electronic,mechanical,photocopying,recording,scanningor otherwise,except underthetermsoftheCopyright DesignsandPatentsAct1988orundertheterms ofalicenceissuedbytheCopyrightLicensingAgency,90TottenhamCourtRoad,LondonW1P9HE, UK,withoutthepermissioninwritingofthePublisher OtherWileyEditorialOffices JohnWiley&Sons,Inc.,605ThirdAvenue, NewYork,NY10158-0012,USA WILEY-VCHVerlagGmbH,Pappelallee3, D-69469Weinheim,Germany JacarandaWileyLtd,33ParkRoad,Milton, Queensland4064,Australia JohnWiley&Sons(Asia)PteLtd,ClementiLoop#02-01, JinXingDistripark,Singapore129809 JohnWiley&Sons(Canada)Ltd,22WorcesterRoad, Rexdale,OntarioM9W1L1,Canada BritishLibraryCataloguinginPublicationData AcataloguerecordforthisbookisavailablefromtheBritishLibrary ISBN0471967572 Typesetin9/10ptTimesbyLaserWords,Madras,India PrintedandboundinGreatBritainbyBiddlesLtd,Guildford,Surrey Thisbookisprintedonacid-freepaperresponsiblymanufacturedfromsustainableforestry, inwhichatleasttwotreesareplantedforeachoneusedforpaperproduction. To Sara and Zippi Dedicated to Robert West a pioneer in silicon chemistry and a dear friend Dedicated to Saul Patai teacher, editor and friend Contributing authors WataruAndo DepartmentofChemistry,UniversityofTsukuba,Tsukuba, Ibaraki 305, Japan YitzhakApeloig Department of Chemistry and the Lise-Meitner Minerva Center for Computational Quantum Chemistry, Technion Israel Institute of Technology, Haifa 32000, Israel D.A.(‘Fred’) Armitage DepartmentofChemistry,King’sCollegeLondon,Strand, London,WC2R 2LS, UK NorbertAuner Fachinstitut fu¨r Anorganische und Allgemeine Chemie, Humboldt-Universita¨t zu Berlin, Hessische Str. 1 2, D-10115 Berlin, Germany DavidAvnir Institute of Chemistry, The Hebrew University of Jerusalem, Jerusalem 91904, Israel AlanR.Bassindale Department of Chemistry, The Open University, Milton Keynes, MK7 6AA, UK RosaBecerra Instituto de Quimica Fisica ‘Rocasolano’, C/Serrano 119, 28006 Madrid, Spain Johannes Belzner Institut fu¨r Organische Chemie der Georg-August- Universita¨t Go¨ttingen, Tammannstrasse 2, D-37077 Go¨ttingen,Germany M. B.BoisenJr DepartmentofMaterialsScienceandEngineering,Virginia Tech, Blacksburg, VA 24061, USA Mark Botoshansky Department of Chemistry, Technion Israel Institute of Technology,Haifa 32000,Israel A.G. Brook LashMillerChemicalLaboratories,UniversityofToronto, Toronto, Ontario M5S 3H6, Canada C.Chatgilialoglu I. Co. C. E. A., Consiglio Nazionale delle Ricerche, Via P. Gobetti 101, 40129 Bologna, Italy Buh-LuenCheng Department of Chemistry, TsingHuaUniversity,Hsinchu, Taiwan 30043,Republic of China NamiChoi DepartmentofChemistry,UniversityofTsukuba,Tsukuba, Ibaraki 305, Japan ErnestW.Colvin Department of Chemistry, University of Glasgow, Glasgow,G12 8QQ, UK vii viii Contributingauthors UweDehnert Institut fu¨r Organische Chemie der Georg-August- Universita¨t Go¨ttingen, Tammannstrasse 2, D-37077 Go¨ttingen,Germany RobertDrake DowCorningLtd,CardiffRoad,Barry,SouthGlamorgan, CF63 2YL, UK JacquesDubac He´te´rochimie Fondamentale et Applique´, ESA-CNRS 5069, Universite´ Paul-Sabatier, 118 route de Narbonne, 31062 ToulouseCedex, France Moris S.Eisen Department of Chemistry, Technion Israel Institute of Technology,Kiryat Hatechnion, Haifa 32000, Israel C.Ferreri DepartimentodiChimicaOrganicaeBiologica,Universita` di Napoli ‘Federico II’, Via Mezzocannone 16, 80134 Napoli,Italy Toshio Fuchigami Department of Electrochemistry, Tokyo Institute of Technology, 4259 Nagatsuta, Midori-ku, Yokohama 226, Japan PeterP.Gaspar Department of Chemistry, Washington University, St Louis,Missouri 63130-4899,USA ChristianGue´rin Chimie Mole´culaire et Organisation du Solide, UMR- CNRS5637,Universite´ MontpellierII,PlaceE. Bataillon, 34095 MontpellierCedex 5, France G. V.Gibbs DepartmentofMaterialsScienceandEngineering,Virginia Tech, Blacksburg, VA 24061, USA T. Gimisis I. Co. C. E. A., Consiglio Nazionale delle Ricerche, Via P. Gobetti 101, 40129 Bologna, Italy SimonJ.Glynn Department of Chemistry, The Open University, Milton Keynes, MK7 6AA, UK NormanGoldberg Technische Universita¨t Braunschweig, Institut fu¨r Organische Chemie, Hagenring 30, D-38106 Braunschweig, Germany EdwinHengge (Deceased) ReubenJih-RuHwu Department of Chemistry, TsingHuaUniversity,Hsinchu, Taiwan 30043,Republic of China Jo¨rgJung Institut fu¨r Organische Chemie der Justus-Liebig Universita¨t Giessen, Heinrich-Buff-Ring 58, D-35392 Giessen, Germany PeterJutzi Faculty of Chemistry, University of Bielefeld, Universita¨tsstr.25, D-33615 Bielefeld, Germany YoshioKabe DepartmentofChemistry,UniversityofTsukuba,Tsukuba, Ibaraki 305, Japan Menahem Kaftory Department of Chemistry, Technion Israel Institute of Technology,Haifa 32000,Israel InnaKalikhman Department of Chemistry, Ben-Gurion University of the Negev, Beer Sheva 84105, Israel MosheKapon Department of Chemistry, Technion-Israel Institute of Technology,Haifa 32000,Israel Contributingauthors ix Miriam Karni Department of Chemistry and the Lise-MeitnerMinerva Center for Computational Quantum Chemistry, Technion Israel Institute of Technology, Haifa 32000, Israel MitsuoKira Department of Chemistry, Graduate School of Science, Tohoku University,Aoba-ku, Sendai 980-77, Japan Sukhbinder S.Klair Department of Chemistry, Loughborough University, Loughborough,Leicestershire, LE11 3TU, UK LisaC.Klein Ceramics Department, Rutgers The State University of New Jersey, Piscataway, New Jersey 08855-0909,USA DanielKost Department of Chemistry, Ben-Gurion University of the Negev, Beer Sheva 84105, Israel Takahiro Kusukawa DepartmentofChemistry,UniversityofTsukuba,Tsukuba, Ibaraki 305, Japan R.M. Laine Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109-2136,USA DavidLevy Instituto de Ciencia de Materiales de Madrid, C.S.I.C., Cantoblanco, 28049 Madrid, Spain LarryN.Lewis GE Corporate Research and Development Center, Schenectady, NY 12309,USA ZhaoyangLi DepartmentofChemistry,StateUniversityofNewYorkat Stony Brook, Stony Brook, New York 11794-3400,USA PaulD.Lickiss Department of Chemistry, Imperial College of Science, Technology and Medicine, London,SW7 2AY, UK Shiuh-TzungLiu Department of Chemistry, National Taiwan University, Taipei, Taiwan 106 Tien-YauLuh Department of Chemistry, National Taiwan University, Taipei, Taiwan 106 GerhardMaas Abteilung Organische Chemie I, Universita¨t Ulm, Albert- Einstein-Allee11, D-89081 Ulm, Germany IainMacKinnon DowCorningLtd,CardiffRoad,Barry,SouthGlamorgan, CF63 2YL, UK SvetlanaKirpichenko Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St, 664033 Irkutsk, Russia ChristophMaerker Laboratoire de Chimie Biophysique, Institut Le Bel, Universite´ Louis Pasteur, 4 rue Blaise Pascal, F-67000 Strasbourg, France Gu¨nther Maier Institut fu¨r Organische Chemie der Justus-Liebig Universita¨t Giessen, Heinrich-Buff-Ring 58, D-35392 Giessen, Germany Michael J.McKenzie Department of Chemistry, Loughborough University, Loughborough,Leicestershire, LE11 3TU, UK AndreasMeudt Institut fu¨r Organische Chemie der Justus-Liebig Universita¨t Giessen, Heinrich-Buff-Ring 58, D-35392 Giessen, Germany

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