title: Oxidation of α-trifluoromethyl alcohols using a recyclable oxoammonium salt.
abstract: A simple, mild method for the oxidation of α-trifluoromethyl alcohols to trifluoromethyl ketones (TFMKs) using the oxoammonium salt 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (1) is described. Under basic conditions, oxidation proceeds rapidly and affords good to excellent yields of TFMKs, without concomitant formation of the hydrate. The byproduct of the oxidation, 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinyloxy (1c), is easily recovered and can be conveniently reoxidized to regenerate the oxoammonium salt.
authors.affiliation: Department of Chemistry, University of Connecticut, 55 North Eagleville Road, Storrs, Connecticut 06269-3060, USA.
authors.forename: Christopher B
authors.initials: CB
authors.lastname: Kelly
authors.forename: Michael A
authors.initials: MA
authors.lastname: Mercadante
authors.forename: Trevor A
authors.initials: TA
authors.lastname: Hamlin
authors.forename: Madison H
authors.initials: MH
authors.lastname: Fletcher
authors.forename: Nicholas E
authors.initials: NE
authors.lastname: Leadbeater
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D001881:Borates / Q000737:chemistry*; D003497:Cyclic N-Oxides / Q000737:chemistry*; D000432:Methanol / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010880:Piperidines / Q000737:chemistry*; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*; D012492:Salts / Q000737:chemistry*
chemical_list: C579777:4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate; D000438:Alcohols; D001881:Borates; D003497:Cyclic N-Oxides; D010880:Piperidines; D000644:Quaternary Ammonium Compounds; D012492:Salts; C534495:trifluoromethanol; D000432:Methanol