N,S-substituted nitrodienes from naphthylthiosubstituted nitrodienes and S-, S,S-substituted dienes from hexachloro-1,3-butadiene

Abstract

Mono(thio)substituted dienes 1 gave compounds 3a-c, 7, 9, and 11 on reaction with pipe-razine derivatives in dry ether. N,S-substituted nitrodiene 5 was obtained from the reaction of 1 with 1,4-dioxospriol 4. Hexachlorobutadiene 12 in a water-ethanol mixture in the presence of sodium hydroxide reacted with ethyleneglycol bismercaptoacetate 13 to give thiosubstituted thioethers 14 and 15.