Thiocyanogen chloride reacts rapidly with ethylene, cis- and trans-but-2-ene, cyclohexene, and trans-Δ2-octalin in the presence of a radical inhibitor in acetic acid in the dark to yield α-chloro-β-thiocyanates and α-acetoxy-β-thiocyanates. The reaction is trans stereospecific. A heterolytic mechanism, involving a two-step, kinetically controlled addition and the formation of a cyano-sulphonium ion intermediate [e.g. (VIII)] is suggested.
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Journal of the Chemical Society, Perkin Transactions 1
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