N,S-, S-, S,S-, 2 -Substituted Dienes from Halo-1,3-Butadienes
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 H 2 SO 4 and KBr. Compounds 9 and 11 gave in the reaction with m-CPBA in chloroform 10 , 12 , and 13 , respectively.
Keywords: Hexachloro-1,3-butadiene; piperazine; sulfone; sulfoxide; thioether, N,S-thiosubstituted nitrodiene; thiol
Document Type: Research Article
Affiliations: Department of Chemistry, Istanbul University, Avcilar, Istanbul, Turkey
Publication date: 01 April 2006
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