Abstract
Abstract The cyclic sulfoxides, thiane 1-oxide, 4-chlorothiane 1-oxides, and 4-phenylthiane 1-oxides, were brominated with a mixture of bromine and N-bromosuccinimide in the presence of pyridine. The stereoformulas of the products, together with those of the isomers with an inverted sulfoxide configuration, were determined by means of the IR and NMR spectral data and by a comparison of the Rf-values in the tic. As a result, it has been revealed that the bromination reaction gives products in which a bromine atom is introduced stereospecifically at a trans-position to the sulfinyl lone pair, in a manner similar to that of the chlorination reaction reported previously. The same mechanism as in the chlorination is proposed for the main reaction course.
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