Preparation and reactions of 5-Aryl-1,4,2-dithiazolium salts

Article abstract of DOI:10.1246/bcsj.63.2933

S-Thioaroylsulfenamides (ArCSSNH₂), formed by reaction of ArCSS-Na⁺ with hydroxylamine-O-sulfonic acid, were aroylated or acylated to give N-aroyl- or N-acyl-S-thioaroylsulfenamides, respectively, which were then cyclized with dehydration to afford 3-substituted 5-aryl-1,4,2-dithiazolium salts. The behavior of 3,5-diphenyl-1,4,2-dithiazolium Perchlorate toward nucleophiles such as active methylene and amino compounds was studied systematically. The reaction can be classified into two cases depending on fission modes of initial adducts, i.e., ring opening-ring closure reaction (Path B) and fragmentation of dithiazole ring (Path C), and in some cases the initial adducts were isolated.