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

G.D. Allen, M.C. Buzzeo, L.G. Davies, Constanza Villagran, Christopher Hardacre, R.G. Compton

Research output: Contribution to journalArticlepeer-review

37 Citations (Scopus)

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
JournalJournal of Physical Chemistry B
Volume108
Issue number41
Publication statusPublished - 14 Oct 2004

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry

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