Abstract
Abstract The cyclic sulfoxides, thiane 1-oxide, cis- or trans-4-chlorothiane 1-oxide, and cis- or trans-4-phenylthiane 1-oxide, were chlorinated with t-butyl hypochlorite, sulfuryl chloride, and chlorine in the presence of potassium acetate or pyridine. The stereoformulas of the products, together with those of the isomers having an inverted sulfoxide configuration, were determined by means of the IR and NMR spectral data and the Rf-values in the tlc. Consequently, it has been found that chlorination occurs when the sulfinyl oxygen is equatorial and that chlorine is always introduced at a trans-position to the sulfinyl lone pair to give rise to the cis-products. A mechanism accommodating these results is proposed. The conformation of the substituted thiane 1-oxide rings is also discussed.
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