CHARACTERIZATION AND STABILITY OF CYCLIC DISULFIDES AND CYCLIC DIMERIC BIS(DISULFIDES)

Article abstract of DOI:10.1016/0040-4020(89)80036-5

This paper describes the preparation of cyclic bis(disulfide) dimers derived from trans-2-butene-1,4-dithiol and cis-1,2-cyclohexane dithiol and the cyclic tris(disulfide) dimer of 1,3,5-tris(mercaptomethyl)benzene by high dilution oxidation of the thiols with iodine.The stability toward ring-opening polymerization of these three new cyclic disulfides and of nine previously reported cyclic disulfides was tested by heating the disulfide with a catalytic amount of sodium methanethiolate.None of the cyclic bis(disulfides) were stable with respect to polymerization under these conditions.The results of these experiments, together with literature reports concerning the stability of similar disulfides, indicate that few simple alkyl disulfides are thermodynamically stable in cyclic form.