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

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 7 pi radicals.