Reactions of 2-nitropolyhalodienes with S,S-, O,S- and N,S-nucleophiles to 1,3-oxathiolane, 1,3-thiazolidine and 1,3-dithane and thioether compounds

Abstract

2-Nitro-1,3-butadiene (1) has yielded 1,3-Oxathiolane when reacted with HS-CH2-CH2-OH in Ethanol in the presence of NaOH. Mono(thio)substituted butadiene compounds 4a-c and 4i were obtained from 1 and thiols (3a-c, 3i). 2-Nitroperhalo-1,3-butadiene (5), when reacted with (3c-t) thiols, gave compounds 7c-l and 8e. 1,3-Thiazolidine 6 was obtained from the reaction of 2-amino-ethanol hydrochloride with compound 5 in the presence of ethanol and sodium hydroxide. Compounds 9, 10 and 11 were obtained by stirring of the compound 5 with an ethanolthiol for a long time. 1,3-Dithiane compound 15 with a heterocyclic structure and thioether compounds 13 and 14 were also obtained from the reaction of 1 with dithiols.