Hydroperoxide oxidation of azomethines and alkylarenes catalyzed by ebselen

Abstract

2-Phenyl-1,2-benzisoselenazol-3(2H)-one (ebselen), known as glutathione peroxidase mimic, is found as an efficient catalyst for hydrogen peroxide and tert-butyl hydroperoxide oxidation of the azomethine group in azines, aldoximes, and methyl or methylene group in alkylarenes. Depending on the substrate used and the reaction conditions, the major products are aldehydes, ketones, carboxylic acids or their derivatives. It is postulated that ebselen is involved in the free-radical oxidation mechanism.