The chemistry of Hydroxylamines, Oximes and Hydroxamic Acids Part 1 Editedby ZVI RAPPOPORT TheHebrewUniversity,Jerusalem and JOEL F. LIEBMAN DepartmentofChemistryandBiochemistry, UniversityofMaryland,BaltimoreCounty 2009 A John Wiley and Sons, Ltd., Publication  AnInterscience Publication The chemistry of Hydroxylamines, Oximes and Hydroxamic Acids PataiSeries:TheChemistryofFunctionalGroups AseriesofadvancedtreatisesfoundedbyProfessorSaulPataiandunderthegeneral editorshipofProfessorZviRappoport ThePataiSeriespublishescomprehensivereviewsonallaspectsofspecific functionalgroups.Eachvolumecontainsoutstandingsurveysontheoreticaland computationalaspects,NMR,MS,otherspectroscopicmethodsandanalytical chemistry,structuralaspects,thermochemistry,photochemistry,syntheticapproaches andstrategies,syntheticusesandapplicationsinchemicalandpharmaceutical industries,biological,biochemicalandenvironmentalaspects. Todate,120volumeshavebeenpublishedintheseries. RecentlyPublishedTitles ThechemistryoftheCyclopropylGroup(Volume2) ThechemistryoftheHydrazo,AzoandAzoxyGroups(Volume2,2parts) ThechemistryofDouble-BondedFunctionalGroups(Volume3,2parts) ThechemistryofOrganophosphorusCompounds(Volume4) ThechemistryofHalides,Pseudo-HalidesandAzides(Volume2,2parts) ThechemistryoftheAmino,NitroandNitrosoGroups(2volumes,2parts) ThechemistryofDienesandPolyenes(2volumes) ThechemistryofOrganicDerivativesofGoldandSilver ThechemistryofOrganicSiliconCompounds(2volumes,4parts) ThechemistryofOrganicGermanium,TinandLeadCompounds(Volume2,2parts) ThechemistryofPhenols(2parts) ThechemistryofOrganolithiumCompounds(2volumes,3parts) ThechemistryofCyclobutanes(2parts) ThechemistryofPeroxides(Volume2,2parts) ThechemistryofOrganozincCompounds(2parts) ThechemistryofAnilines(2parts) ThechemistryofOrganomagnesiumCompounds(2parts) ForthcomingTitles ThechemistryofMetalEnolates ThechemistryofOrganocopperCompounds ThePataiSeriesOnline Startingin2003thePataiSeriesisavailableinelectronicformatonWiley InterScience.Allnewtitleswillbepublishedasonlinebooksandagrowinglistofoldertitles willbeaddedeveryyear.ItistheultimategoalthatalltitlespublishedinthePatai Serieswillbeavailableinelectronicformat. FormoreinformationseeunderOnlineBookson: www.interscience.wiley.com R O C N C N C N OH OH OH The chemistry of Hydroxylamines, Oximes and Hydroxamic Acids Part 1 Editedby ZVI RAPPOPORT TheHebrewUniversity,Jerusalem and JOEL F. LIEBMAN DepartmentofChemistryandBiochemistry, UniversityofMaryland,BaltimoreCounty 2009 A John Wiley and Sons, Ltd., Publication  AnInterscience Publication Copyright2009 JohnWiley&SonsLtd,TheAtrium,SouthernGate,Chichester, WestSussexPO198SQ,England Telephone(+44)1243779777 Email(forordersandcustomerserviceenquiries):[email protected] VisitourHomePageonwww.wileyeurope.comorwww.wiley.com AllRightsReserved.Nopartofthispublicationmaybereproduced,storedinaretrievalsystemortransmitted inanyformorbyanymeans,electronic,mechanical,photocopying,recording,scanningorotherwise,except underthetermsoftheCopyright,DesignsandPatentsAct1988orunderthetermsofalicenceissuedbythe CopyrightLicensingAgencyLtd,90TottenhamCourtRoad,LondonW1T4LP,UK,withoutthepermissionin writingofthePublisher.RequeststothePublishershouldbeaddressedtothePermissionsDepartment,John Wiley&SonsLtd,TheAtrium,SouthernGate,Chichester,WestSussexPO198SQ,England,oremailedto [email protected],orfaxedto(+44)1243770620. 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QD305.A7C442008 547—dc22 2008046989 BritishLibraryCataloguinginPublicationData AcataloguerecordforthisbookisavailablefromtheBritishLibrary ISBN978-0-470-51261-6 Typesetin9/10ptTimesbyLaserwordsPrivateLimited,Chennai,India PrintedandboundinGreatBritainbyBiddlesLimited,KingsLynn,Norfolk Thisbookisprintedonacid-freepaperresponsiblymanufacturedfromsustainableforestry inwhichatleasttwotreesareplantedforeachoneusedforpaperproduction. Dedicated to the memory of Professor Tuvia Sheradsky and to + Kifele bat TC C, and Moische ben A * C Contributing authors EdgarsAbele Latvian Instituteof Organic Synthesis,Riga, LV1006, Latvia. Fax: +371-7550338;e-mail: [email protected] YacovAshani Department of Neurobiology,The Weizmann Instituteof Science, Rehovot 76100, Israel. Fax: +972-8-9346017; e-mail: [email protected] YanivBarda Department of Organic Chemistry, Weizmann Instituteof Science, P.O. Box 26, Rehovot 76100,Israel. Fax: +972-8-9342917;e-mail: [email protected] HaraldBrand LMU Munich,Butenandt-Str. 5–13,81377 Mu¨nchen, Germany. e-mail: [email protected] ErwinBuncel Department of Chemistry, Queen’s University,Kingston, Ontario K7L 3N6, Canada. Fax: +1-613-533-6669; e-mail: [email protected] MarvinCharton Chemistry Department, School of Liberal Arts and Sciences, Pratt Institute,Brooklyn, NY 11205,USA. Fax: +1-718-722-7706;email: [email protected] JacquesFernandesDias Departamento de Qu´ımica e Ambiental, Faculdade de Tecnologia, Universidadedo Estado do Rio de Janeiro, Rodovia Presidente Dutra km 298—Po´lo Industrial, Resende, RJ, 27537-000,Brazil. Fax: +55-24-3354-7875; e-mail: [email protected] EnderErdik Ankara UniversityScience Faculty, Department of Chemistry, Bes¸evler, Ankara 06100, Turkey.Fax: +90-312-223-23-95;e-mail: [email protected] CliffordE.Felder Department of Organic Chemistry, Weizmann Instituteof Science, P.O. Box 26, Rehovot 76100, Israel. Fax: +972-8-9342917;e-mail: [email protected] CarloGalli IMC-CNR Sezione Meccanismi di Reazione, c/o Dipartimento di Chimica, Universita` ‘La Sapienza’, 00185 Roma, Italy. Fax: +39-06-490421;e-mail: [email protected] GiampaoloGiacomelli Universita` degli Studi di Sassari, Dipartimento di Chimica, via Vienna 2, 07100-Sassari, Italy. Fax: +39-079-212069;e-mail: [email protected] vii