title: Oxidation of oximes to nitrile oxides with hypervalent iodine reagents.
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.
authors.affiliation: Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver BC V6T 1Z1, Canada.
authors.forename: Brian A
authors.initials: BA
authors.lastname: Mendelsohn
authors.forename: Shelley
authors.initials: S
authors.lastname: Lee
authors.forename: Simon
authors.initials: S
authors.lastname: Kim
authors.forename: Florian
authors.initials: F
authors.lastname: Teyssier
authors.forename: Virender S
authors.initials: VS
authors.lastname: Aulakh
authors.forename: Marco A
authors.initials: MA
authors.lastname: Ciufolini
mesh_terms: D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D006847:Hydrocarbons, Iodinated / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D010084:Oxidation-Reduction; D010087:Oxides / Q000737:chemistry; D010091:Oximes / Q000737:chemistry*
chemical_list: D006847:Hydrocarbons, Iodinated; D009570:Nitriles; D010087:Oxides; D010091:Oximes