Formation and GC-MS characterization of unusual cyclic sulfides

In connection with another project involving the cleavage of the thiirane r ing of cyclohexene episulfide in the presence of trifluoromethylthiocopper, the presence of several unusual cyclic sulfides (5-10, Fig. 1) was observe d both in the reaction product and the starting material itself. The format ion of these compounds has been rationalized on the presence and participat ion of the thiyl radical species. Details pertaining to their formation and characterization based on their mass spectral fragmentation behavior are p resented in this communication.