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1、REVIEW1979ApplicationsofTEMPOinSynthesisApplicationsofTEMPOinSynthesisThomasVogler,ArmidoStuder*Organisch-ChemischesInstitut,WestfälischeWilhelms-UniversitätMünster,Corrensstraße40,48149Münster,GermanyFax+49(251)8336523;E-mail:studer@uni-muenster.deReceived3March2008;revised15April2008thenbelieve
2、dtobeunstable.5However,themostpromi-Abstract:ThisreviewdescribesthebroadapplicationofTEMPOnentmemberofthisclassofcompoundsisthe2,2,6,6-tet-anditsderivativesinorganicsynthesis.Variousreactionsincludingoxidationofalcohols,sulfidesandorganometalliccompoundsareramethylpiperidine-N-oxylradical(TEMPO).
3、Thisdiscussed.Moreover,theuseofTEMPOasastoichiometricorcat-nitroxidewasfirstsynthesizedbyLebedevandKazar-alyticcooxidantinvarioustransition-metal-mediatedreactionsisnovskiiin1959(Figure1).6presented.TheapplicationofTEMPOasacarbon-radicaltrappingreagentincascadereactionsisdiscussed.Finally,therevi
4、ewarticleHNfocusesontheapplicationofTEMPO-derivedalkoxyaminesasNHthermalcarbon-radicalprecursorsinsynthesisandinpolymerKO3SSO3KNHchemistry.NNNNOOOO1Nitroxides2Oxidations345TEMPO2.1OxidationofAlcoholsFigure1Stablenitroxides2.2OxidationofSulfidesandHydrogenAbstractions3TEMPOasTrappingReagent4Reacti
5、onofTEMPOwithOrganometallicCompoundsManynitroxidesarestableatroomtemperatureandbe-5Carbon–OxygenBondHomolysisofAlkoxyamineslongtotheclassofpersistentradicals.7Thedelocalization6Conclusionsenergyfortheunpairedelectronisapproximately120kJ/Keywords:nitroxides,oxidations,radicalchemistry,dominoreac-m
6、ol(three-electronN–Obond).8Thestericdemandofthetions,polymerizationssubstituentsofdialkylnitroxidesshieldsthenitroxidefunctionalityandcontributestoitskineticstability.Ni-troxidesbearingheteroatomsubstituentsorarylsubstitu-1Nitroxidesentsarelessstablethanthealkyl-substitutednitroxides.Adelocalizat
7、ionoftheradicalintothearomaticringweak-Nitroxylradicals,alsocallednitroxides,areN,N-disubsti-ensthenitrogen–oxygenbondindiaryl-substitutedni-troxides.1,9tutedNOradicalswithanunpairedelectrondelocalizedbetweenthenitroge
