Supramolecular Oxidation of Anilines Using Hydrogen Peroxide as Stoichiometric Oxidant

Abstract

6A,6D-Di-O-(propan-2-on-1,3-diyl) alpha-cyclodextrin-6A,6D-dicarboxylate (2alpha) and 6A,6D-di-O-(propan-2-on-1,3-diyl) beta-cyclodextrin-6A,6D-dicarboxylate (2beta) were found to catalyze the oxidation of aromatic amines in the presence of hydrogen peroxide. The products were the corresponding nitro compounds or in some cases azo-, azoxy-, or other dimerization products. The catalysis was found to follow enzyme kinetics giving a rate increase (kcat/kuncat) of up to 1100 in the best case.