SYNTHETIC, STRUCTURAL AND ELECTROCHEMICAL STUDIES ON THE 1,2-DITHIOLE-3-THIONE SYSTEM - PREPARATION AND REACTIONS OF THE 5,6-DIHYDRO-1,2-DITHIOLO[4,5-B][1,4]DITHIIN-3-IUM CATION

The synthesis. X-ray crystal structure and some reactions of 1,2-dithiole-3-thione derivative 8 are reported. The structure of thione 8 is characterised by a remarkable three-dimensional network of close, non-bonded, S---S interactions. Compound 8 is efficiency converted into the 1,2-dithiolium cation salt 11 by sequential reaction with meta-chloroperoxybenzoic acid and sodium iodide. Cation salt 11 reacts with aqueous ammonia in the presence of iodine to afford isothiazole derivative 18 in high yield the mechanism proposed for this reaction proceeds via 1,2,3-dithiazine derivative 17. The solution electrochemistry of the title thione, and related compounds, has been studied by cyclic voltammetry.