Free-Radical Thiylation of Di-, Tri-, and Tetrachloroethylenes and 1,1,2-Trichloropropene with Organyl Thiols and Diaryl Disulfides

UV-Irradiation and benzoyl peroxide initiated radical reactions of the title ethenes with aliphatic and aromatic thiols and diaryl disulfides are presented. From these reactions individual unsaturated sulfides RSCX[dbnd]CYZ (X, Y, Z = H, Cl, CH3) or mixtures of the above isomeric sulfides and saturated sulfides RSCXX′CX″X″′Y (X, X′, X″, X″′ = H, Cl; Y = H, Cl, CH3) have been obtained. The reaction features in each given case and differences in the reaction course for thiols and disulfides are discussed. Reaction mechanisms explaining the differences in the process in each particular case are suggested.