Oxidation of Alcohols with tert-Butyl Hydroperoxide and Diaryl Diselenide

Article abstract of DOI:10.1021/jo00344a017

Treatment of alcohols with tert-butyl hydroperoxide in the presence of diaryl diselenide in refluxing benzene gives the corresponding aldehydes or ketones.Although some allylic alcohols undergo oxidation in the presence of 10-15 mol percent of bis(p-chlorophenyl) diselenide, use of 0.5 equiv of bis(2,4,6-trimethylphenyl) diselenide gives satisfactory results in almost all cases.The procedure can be used for selective oxidation of alcohols bearing a phenylthio or phenylseleno group, which usually survives the reaction conditions to give the corresponding carbonyl compounds.