NEW THIOETHERS FROM 2-NITROPENTACHLORO-1,3-BUTADIENE AND SULFONYL-1,3-BUTADIENES AND SULFINYL-1,3-BUTADIENES FROM TETRAKIS(ORGANYLTHIO)-1,3-BUTADIENES AND TRIS(ORGANYLTHIO)-1,3-BUTADIENES

2-Nitropentachlorobutadiene (1) gives 3a-b, 3d and 4c by the reaction with thiols in DMF containing triethylamine. 5a-b, 6c and 6d are prepared by the reaction of compound 1 with thiols in EtOH containing sodium hydroxide. 7c and 7d are formed by the reaction of compound 1 with thiols in the absence of a solvent. Poly(thio)substituted compounds (8, 10, 12) have been oxidized by 3-chloroperbenzoic acid (m-CPBA) in chloroform at 0 degrees C. 9a, b and c sulfonyl compounds have been obtained from 8a, b, c and m-CPBA. Compound 13a containing sulfone and sulfoxide groups was prepared from compound 12a by oxidation under the same conditions. Sulfinyl compounds 10a, b, c give compounds 11a, b, c by reaction with m-CPBA.