New transformation of 1,3-oxathiolane-2-thione into 1,3-dithiolan-2-one via polymerization and depolymerization

This article deals with the cationic and anionic depolymerization of polydi thiocarbonate, which was synthesized by cationic polymerization of 5-phenox y-methyl-1,3-oxathiolane-2-thione (1) using methyl triflate as the initiato r. The cationic depolymerization of the obtained polymer was carries out in the presence of 5-20 mol-% of methyl triflate or triflic acid catalyst in chlorobenzene at 60 degreesC for 96 h to afford 4-phenoxymethyl-1,3-dithiol an-2-one (2) in 35-83% yield. The anionic depolymerization of the polymer w as carried out in the presence of 5 mol-% of triethylamine or potassium ter t-butoxide at 20 degreesC for 24 h to afford 2 in 85-100% yield.