N,S-, S-, S,S-, 2-substituted dienes from halo-1,3-butadienes

Abstract

Mono(thio) substituted dienes 1 gave 3a-g, 5, and 7 with piperazine derivatives in dichloromethane. Hexachlorobutadiene 14 in a water-ethanol mixture in the presence of sodium hydroxide reacted with thiol 15 to give the mono(thio) substituted thioether 16 and di(thio) substituted thioether 17. 18 was obtained from the reaction of 16 with m-CPBA in chloroform. 9 was obtained from the reaction of l,2,3,4,4-pentachloro-(1-2-hydroxyethylthio)-1,3- butadiene 8 with 47% HI, and 11 was synthesized from the reaction of 8 with concentrated H2SO4 and KBr. Compounds 9 and 11 gave in the reaction with m-CPBA in chloroform 10, 12, and 13, respectively.