Synthesis of Novel Thioethers and Sulfoxide Compounds

Abstract

10 Cl (Br)Cl Cl Br S Br O 12 R 2 5 R 1 S R 1 S H Cl Cl Cl 4 Cl H Cl Cl Cl R 1 S Abstract Thiosubstituted butadiene and butenyne compounds were synthesized from the reactions of 1,1,3,3,4,4-hexachloro-1-butene or 1,1,2,4,4-pentachlorobuta-1,3-diene with different thiols in EtOH/H 2 O solution of NaOH. Tris(thio)substituted butadiene compound was treated with potassium tert-butoxide to obtain tris(thio)substituted butatrienyl halide compound. The novel sulfoxide compounds were synthesized from the reactions of polyhalobutadiene compounds with aliphatic thiols in CHCl 3 with m-CPBA at 0 • C. The structures of the novel compounds were characterized by micro analysis, FT-IR, 1 H-NMR, 13 C-NMR, and MS.

Synthesis of (Thio)substituted -1,3-Butadienes and -Butenynes

“…Reactions of polyhalo-dienes and -butenes with thiols or amines have been previously reported by Ibis and co-workers and Roedig and coworkers (12)(13)(14)(15)(16)(17)(18)(19)(20)(21)(22)(23)(24)(25)(26). Yoshimatsu et al reported the preparation of 2-sulfonyl-1-buten-3-ynes and their reactions with nucleophiles (9).…”

“…It is reported by our laboratory, that the reaction between 1 and different thiols under mild conditions results the formation of thiosubstituted 1,3-butadienes/butenynes (12)(13)(14). Among them, in 2010 (19) and 2016 (20), we reported that some mono-, bis-, tris-and tetrakis-substituted butenynes, butadienes or buta-1,2,3-trienes and their halogenation (iodination/bromination) and oxidation of some butadienes to their corresponding sulfoxides or sulfones.…”