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Issue 0, 1973
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Pseudohalogen chemistry. Part I. Heterolytic addition of thiocyanogen chloride to some symmetrical alkenes and cycloalkenes

Abstract

Thiocyanogen chloride reacts rapidly with ethylene, cis- and trans-but-2-ene, cyclohexene, and trans2-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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Article type: Paper
DOI: 10.1039/P19730000281
Citation: J. Chem. Soc., Perkin Trans. 1, 1973, 281-284
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    Pseudohalogen chemistry. Part I. Heterolytic addition of thiocyanogen chloride to some symmetrical alkenes and cycloalkenes

    R. G. Guy and I. Pearson, J. Chem. Soc., Perkin Trans. 1, 1973, 281
    DOI: 10.1039/P19730000281

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