New Perchlorobutadienyl Sulfanes

Abstract

Hexachlorobutadiene 1 reacts with 3-mercapto-1-hexanol in water-ethanol mixture in the presence of sodium hydroxide to give the new monosubstituted thioether 3-(perchlorobuta-1,3-dienyl-thio)-hexan-1-ol 3a and the disubstituted thioether 3,3' -(perchlorobuta-1,3-diene-1,4-diyl) bis(sulfane-diyl)-dihexan-1-ol 4a. 1-Chlorohexan-3-yl-pentachlorobutadienyl-sulfide 5a, 2-chloroethyl-penta-chlorobutadienyl-sulfide 5b, 2-chloropropyl-pentachlorobutadienyl-sulfide 5c and 1,2,3,4-tetra-chlorobuta-1,4-bis(2-chloroethylsulfanyl)-buta-1,3-diene 6b were obtained from the reaction of 3a-c and 4b with SOCl2 in pyridine. The derivatives 8b-k and 9a were synthesized from the reaction of componds 5b and 5c in water-ethanol mixture in the presence of sodium hydroxide with the corresponding thiol, respectively.