Treatment of alkenes with ‘thiocyanogen bromide’ prepared from equimolar amounts of bromine and thallium(I) thiocyanate in wet chloroform, gives moderate to high yields of vic-bromothiocyanates. The addition proceeds by an ionic mechanism involving nucleophilic attack of a bromide ion on an S-cyanothiiranium cation. Unlike vic-iodothiocyanates, the vic-bromothiocyanates are not readily isomerized to the corresponding vic-halogenoisothiocyanates.
R. C. Cambie, D. S. Larsen, P. S. Rutledge and P. D. Woodgate, J. Chem. Soc., Perkin Trans. 1, 1981, 58 DOI: 10.1039/P19810000058
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