REACTIONS OF 2-NITROPENTACHLORO-1,3-BUTADIENE WITH THIOLS AND MONO(THIO)-SUBSTITUTED 2-NITROBUTADIENES WITH DITHIOLS

Mono(thio)substituted compounds 3a-g and 3g are prepared by mixing 2-nitropentachlorobutadiene (1) with thiols 2a-g. 2-Nitrodiene 1 gives bis(thio)substituted 4c and tris(thio)substituted 5d by the reaction with the same thiols in EtOH containing sodium hydroxide. Cyclic thioethers 7a-b, acyclic thioether 9a and disulfide derivatives 8a-b are formed by the reaction of 3a with 1,2-ethanedithiol (6a) and 1,3-propanedithiol (6b) in EtOH in the presence of sodium hydroxide.