Thiosulphonic S-esters - 5. Mechanistic aspects of the reaction with chlorotrimethylsilane and sodium iodide

Thiosulfonic S-esters (1) are readily converted to disulfides (2) by chlorotrimethylsilane and sodium iodide. The reaction is shown to proceed through a complex mechanism, and more than one conversion pathway to disulfides must be considered. Evidence is presented for several S-S bond cleavage and reformation reactions involved in the conversion. In view of these results, the mechanistic interpretations proposed for already known reactions of various sulfur compounds with either chlorotrimethylsilane-iodide or iodotrimethylsilane should probably be revised. The behaviour of other reducing agents of thiosulfonates (1) to disulfides (2) was also checked.