Oxidation of oximes to nitrile oxides with hypervalent iodine reagents.
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.
Mendelsohn
Brian A
BA
Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver BC V6T 1Z1, Canada.
Lee
Shelley
S
Kim
Simon
S
Teyssier
Florian
F
Aulakh
Virender S
VS
Ciufolini
Marco A
MA
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*
D006847:Hydrocarbons, Iodinated; D009570:Nitriles; D010087:Oxides; D010091:Oximes