One-pot oxidation polymerization of dithiols, obtained from bifunctional five-membered cyclic dithiocarbonates (4a and 4b) with two equivalents of amines, was studied. The monomers 4a and 4b were synthesized by the reactions of bisphenol A diglycidyl ether and neopentyl glycol diglycidyl ether with carbon disulfide, respectively. Polydisulfides with (M) over bar(n)s 4600-20,200 were obtained quantitatively in the oxidation polymerization of the dithiols obtained in situ by the reactions of 4a with benzylamine, n-butylamine, and piperidine. On the other hand, dithiols obtained from 4b with benzylamine, afforded cyclic disulfides as well as the polydisulfide under similar conditions.