A comparative study on the reactivity of electrogenerated bromine with cyclohexene in acetonitrile and the room temperature ionic liquid, 1-Butyl-3-methylimidazolium bis[(trifluoromethyl)sulfonyl]imide

Gary D. Allen, Marisa C. Buzzeo, Ieuan G. Davies, Constanza Villagrán, Christopher Hardacre, Richard G. Compton

    Research output: Contribution to journalArticlepeer-review

    Abstract

    The reactivity of electrogenerated bromine with cyclohexene has been studied on a platinum microelectrode by linear sweep and cyclic voltammetry in both the room temperature ionic liquid, 1-butyl-3-methylimidazolium bis[(trifluoromethyl)sulfonyl]imide, and the conventional aprotic solvent, acetonitrile. Variation in the voltammetric response was observed in the two solvents, indicating that the bromination reaction proceeded via separate mechanisms. To identify the different products, electrolysis was conducted on the preparative scale and NMR spectroscopy confirmed that while bromination of the organic substrate in the ionic liquid yields trans-1,2-dibromocyclohexane, in acetonitrile, trans-1-(N-acetylamino)-2-bromocyclohexane is instead obtained as the major product. The reaction mechanism for bromination in acetonitrile has been modeled using digital simulation.

    Original languageEnglish
    Pages (from-to)16322-16327
    Number of pages6
    JournalThe Journal of Physical Chemistry Part B: Condensed Matter, Materials, Surfaces, Interfaces & Biophysical
    Volume108
    Issue number41
    DOIs
    Publication statusPublished - 14 Oct 2004

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