Studies on the synthesis of heterocyclic compounds. XVI. Cleavage of 1,3-benzodioxoles and -benzoxathioles by sodium iodide-acyl chloride

The cleavage reaction of ethereal and thioethereal bonds with sodium iodide and acyl chloride has been studied. In all the 1,3-benzodioxoles and -benzoxathioles studied, the opening of the heterocyclic ring with formation of 1,2-diacetoxybenzene or 2-hydroxythiophenol diacetic ester and gem-diiodoalkanes and iodoalkenes has been observed. The structure of newly prepared compounds has been determined by analytical and spectroscopic data or comparison with authentic samples.