New thioethers and disulfide compounds from mono(arylthio)-substituted 2-nitrotetrachloro-1,3-butadiene and new thioethers with butadiene, butyne and butenyne structures from hexachlorobutene

Abstract

2-Nitro-tetrachlor-mono(4-methylphenylthio)-1.3-butadiene (la) in water-ethanol mixture in the presence of sodium hydroxide reacted with 2,2-Oxydiethanethiol (2a) to give heterocyclic thiother 3a, disulfide compound 7a and bis(arylthio)-1,3-butadiene 8a. Compound la from reaction with 1,4,8,11-tetrathiaundecan (2b) in ethanol yielded cyclic thioether 3b, disulfide 5b, 8b and tris(arylthio)-1,3-butadiene 9b compounds. 2-Nitro-tetrachlor-mono(4-chlorphenylthio)-1,3-butadiene (16b) gives 3c, 4c and 6c by the reaction with dithiol 2a in EtOH containing sodium hydroxide. From reaction compound Ib with 2b in EtOH yielded 3d, 10d and 8b compounds. Compounds 12b and 13b, have been obtained from Ib and cystamine in EtOH at room temperature. 14 yielded previously unknown 16a-b, 17a-b, 18a, 17c and 19a-c thioether compounds from reaction with thiols (15a-c). Compound 21 gives 22a, 23a and 24a by the reaction with octanthiol in DMSO.