Two directions of heterocyclization in the reactions of dimethyl bicyclo[2.2.2]oct-5-ene-endo-2,endo-3-dicarboxylate with hetarenesulfenyl chlorides

Abstract

A reaction of dimethyl bicyclo[2.2.2]oct-5-ene-endo-2,endo-3-dicarboxylate with 1,3-benzо- thiazole-2- and 3-methoxycarbonylpyridine-2-sulfenyl chlorides leads to two types of heterocyclization products, which are formed through the ring closure by the oxygen atom of the carbоmethoxy group and/or by the nitrogen atom of the hetaryl fragment of the sulfenylating agent. The product ratio is affected by the medium nature and structural features of sulfenyl chlorides.