Activation of superoxide: Application of peroxysulphur intermediates to organic synthesis

Abstract

For the activation of superoxide anion radical (O2), O2 was reacted with arenesufonyl or arenesulfinyl-chlorides at −20 − 30 °C to generate the corresponding new arenesulfonylperoxy- or arenesulfinylperoxy radical intermediates. These peroxysulfur intermediates show excellent oxidizing abilities for the regioselective epoxidations of olefins, oxidative desulfurizations of thiocarbonyls to carbonyls, cleavages of C=N to C=O and conversion of the benzylic methylene groups to ketones under mild conditions at ca. −-20 °C. The formation of these peroxy intermediates have been also confirmed by the spin trapping studies by ESR. © 1993 IUPAC