The Chemistry of Organic Silicon Compounds, Volume 3

2780 Pages·2001·21.805 MB·English

by  Zvi Rappoport, Yitzhak Apeloig

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
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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