Oxidation of Oximes to Nitrile Oxides with Hypervalent Iodine Reagents
Brian A. Mendelsohn(University of British Columbia), Shelley Lee(University of British Columbia), Simon Kim(University of British Columbia), Florian Teyssier(University of British Columbia), Virender S. Aulakh(University of British Columbia), Marco A. Ciufolini(University of British Columbia)
Cited by 214
Abstract
Iodobenzene diacetate in MeOH containing a catalytic amount of TFA efficiently oxidizes aldoximes to nitrile oxides. The latter may be trapped in situ with olefins in a bimolecular or an intramolecular mode. The new method enables the execution of tandem oxidative dearomatization of phenols/intramolecular nitrile oxide cycloaddition sequences leading to useful synthetic intermediates.