Similarly, when di-n-propyl trisulfide was subjected to photolysis in DMF using a 254 nm light source, formation of the corresponding disulfide was observed within minutes by GC-MS (Figure ). As this reaction presumably generates thiyl (RS•) and perthiyl (RSS•) radicals by homolytic cleavage of the S-S bond of the trisulfide, it is unlikely that such intermediates are featured in the trisulfide metathesis reaction of interest. This experiment also indicates that the trisulfide metathesis is unlikely to be a photochemical process. Finally, it was found that rapid metathesis was observed between dimethyl trisulfide and di-n-propyl trisulfide using N,N-dimethylacrylamide as the solvent (Figure and). Only trisulfide products were observed in the metathesis reaction and no reaction with N,N-dimethylacrylamide was observed. This solvent would be expected to react if thiolates or thiyl radicals were intermediates, but no polymerization or addition to the alkene of N,Ndimethylacrylamide was observed. Together, these results suggest that the S-S metathesis of trisulfides in DMF and related solvents features neither thiolate nor radical intermediates.