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Issue 9, 2000
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Thiocyanation of alkyl halides with alkyl thiocyanates in the presence of quaternary phosphonium halides

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Abstract

Alkyl thiocyanates undergo simple SN2 reactions with the counter ions of quaternary phosphonium salts in nonpolar solvents and thiocyanate ions are liberated as the leaving ion. Depending on the nucleophile, the reaction proceeded irreversibly or reversibly. The reaction of benzyl thiocyanate with azide ions afforded a quantitative yield of benzyl azide. The reactions of alkyl thiocyanates with halide ions gave an equilibrium mixture where the reverse reaction of the alkyl halides produced with the liberated thiocyanate ions took place simultaneously. Thus, thiocyanate–halide exchange reactions between an alkyl thiocyanate and an alkyl halide were possible in the presence of a catalytic amount of a quaternary salt.

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Publication details

The article was received on 02 May 2000, accepted on 14 Jun 2000 and first published on 03 Aug 2000


Article type: Paper
DOI: 10.1039/B003491F
Citation: J. Chem. Soc., Perkin Trans. 2, 2000,0, 1851-1856
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    Thiocyanation of alkyl halides with alkyl thiocyanates in the presence of quaternary phosphonium halides

    N. Ohtani, S. Murakawa, K. Watanabe, D. Tsuchimoto and D. Sato, J. Chem. Soc., Perkin Trans. 2, 2000, 0, 1851
    DOI: 10.1039/B003491F

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