Reaction of thiols with 7-methylbenzopentathiepin.

Polysulfides typically react readily with thiols, thus, reactions of endogenous cellular thiols with the polysulfide linkage in naturally-occuring pentathiepin cytotoxins are likely to be an important aspect of their biological chemistry. Here, it is reported that the reaction of thiols with the pentathiepin ring system initially produces a complex mixture of polysulfides that further decomposes in the presence of excess thiol to yield the corresponding 1,2-benzenedithiol with concomitant production of H(2)S and dimerized thiol. In this reaction, a single molecule of the pentathiepin consumes approximately six equivalents of thiol. The reaction of thiols with the pentathiepin ring system is faster than the analogous reaction involving typical di- and trisulfides.