R. Caputo, C. Ferreri, Giovanni Palumbo
1991
Citations
0
Influential Citations
16
Citations
Journal
Tetrahedron
Abstract
Abstract Ethanediyl S,S-acetal derivatives of cyclohexanone and substituted cyclohexanones are reported to be fast and smoothly converted into 1,4-benzodithians, by concurrent aromatization of the six-member ring and expansion of the five-member sulfur-containing one, under simple treatment with bromine in anhydrous chloroform at room temperature. This conversion represents the first hitherto reported synthetic way leading to 1,4-benzodithians (2) variously substituted at the benzenoid ring. The ready availability of these latter makes the 1,4-benzodithian system itself being regarded as appealing intermediate to obtain, after sulfur replacement or removal, aromatic compounds that cannot be prepared under the usual electrophilic substitution conditions.