Evolution of the pseudo-1,3-dipolar cycloaddition chemistry of SNSMF6 (M = As, Sb) leading to 2,5-dihydroxybenzo-1,3,2-dithiazolylium and 2,7-dicarbonylnaphtha-1,3,2-dithiazolylium salts and their corresponding radicals

Abstract

We report the unprecedented formation of a benzo-fused 1,3,2-dithiazolylium [AsF₆⁻] salt by a one step, quantitative, cycloaddition of SNSAsF₆ with 1,4-benzoquinone. In contrast, the reaction of SNSSbF₆ with 1,4-naphthaquinone results in 2,7-dicarbonylnaphtha-1,3,2-dithiazolylium [SbF₆⁻]. Both were reduced to the corresponding 7π radicals.