Cycloaddition of dimethyl acetylenedicarboxylate with 2-imino-1,3-oxathioles

Abstract

2-Phenylimino-1,3-oxathioles (1) , acting as masked 1,3-dipoles with carbon as the central atom, add dimethyl acetylenedicarboxylate to give aryl propionitriles (4) and dimethyl 2,3-dihydro-3-phenyl-2-'M.

Reaction of Tetraazathiapentalene and Thiadiazolopyrimidine Derivatives with Heterocumulenes: Cycloaddition and Elimination Reactions via Hypervalent Sulfur Intermediates.

“…Ethylene trithiocarbonate [1], Hector's base (4-aryl-3arylmino-5-imino-1,2,4-thiadiazolidines) [2], 4-alkyl-5imino-3-methyl-Δ 2 -1,2,4-thiadiazolines [3], and 2-phenyl-1 , 3 -o x a t h i o l s [4] are known to react with acetylenes to afford ring-opened products through a 1,3-dipolar cycloaddition [5]. These reactions have attracted much attention in connection with the chemistry of 6a-thiathiophtenes [6].…”