Silicon in organosulfur chemistry. Part 3. Disulfide–silyl sulfide interchange. A new aspect of the thiol–disulfide interchange

Abstract

Aryl silyl sulfides (2) undergo interchange reactions with disulfides while, under the same reaction conditions, the corresponding alkyl silyl sulfides are unreactive. Furthermore, the reaction of alkyl aryl disulfides with arylthiosilanes shows a peculiar selectivity in that exchange of the arylthio residues only is observed. This reaction, which represents a new aspect of the well known thiol–disulfide interchange, takes place under mild and neutral conditions. A possible rationalization of the mechanism of this new reaction is also proposed.