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Issue 4, 2002
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Ion pair formation in the addition of protic reagents to alkynes

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Abstract

The reaction of oct-4-yne with 20% trifluoroacetic acid and a variety of relatively weak nucleophiles in methylene chloride was found to produce a mixture of anion incorporated and solvent incorporated products. The rates of these reactions with a range of salt concentrations were found to be proportional to the rates of reaction of simple alkenes under similar conditions. The results are explained by the formation of an intermediate ion pair in contrast to the reactions of alkynes with bromide or iodide which proceeded by a concerted mechanism.

Graphical abstract: Ion pair formation in the addition of protic reagents to alkynes

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Publication details

The article was received on 02 Jan 2002, accepted on 13 Feb 2002 and first published on 27 Feb 2002


Article type: Paper
DOI: 10.1039/B111724F
Citation: J. Chem. Soc., Perkin Trans. 2, 2002,0, 756-758
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    Ion pair formation in the addition of protic reagents to alkynes

    H. M. Weiss, K. M. Touchette and G. Jones, J. Chem. Soc., Perkin Trans. 2, 2002, 0, 756
    DOI: 10.1039/B111724F

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