THIOSULFONIC S-ESTERS - 5. MECHANISTIC ASPECTS OF THE REACTION WITH CHLOROTRIMETHYLSILANE AND SODIUM IODIDE

Article abstract of DOI:10.1016/S0040-4020(01)82088-3

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.