New open-chain or cyclic thioethers with diene, tetraene and hexaene structure from hexachlorobutadiene

Hexachlorobutadiene (1) in water-ethanol mixture in the presence of sodium hydroxide reacted with thiols to give mono(thio)substituted thioethers 7a-e and di(thio)substituted thioethers 8a-e. Heterocyclic thioether 3a, linear chain thioethers 4a, 6a and disulfide compound 5a were obtained from reaction of 1 with 2,2'-oxydiethanethiol in water-ethanol mixture in the presence of sodium hydroxide. Compounds 3b, 4b, 5b and 6b were obtained under the same reaction conditions from 1 and 1,6-hexanedithiol. Compound 1 from reaction in ethanol with 1,9-nonane-(3,7-dithia)dithiol yielded cyclic polythioether 10 and thioether 11 compounds. Disulfone compound 12, sulfone-sulfoxide compound 13 and disulfoxide compound 14 were obtained from the reaction of 4a with 4 moles of m-chloroperbenzoic acid (m-CPBA) in chloroform. 4a gave in the reaction with 2 moles of m-CPBA in chloroform compounds 14 and 15.