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Issue 10, 2002
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Studies of the reactivity of N-heterocyclic carbenes with halogen and halide sources

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Abstract

The reactivity of the N-heterocyclic carbene (NHC) 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene, IMes, with a series of halide sources, including 1,1,1,2,2,2-hexachloroethane, 1,2-dibromoethane and dibromine, has been assessed. These result in the formation of the imidazolium species 1,3-bis(2,4,6-trimethylphenyl)-2-chloroimidazolium chloride, [IMesCl][Cl], 1,3-bis(2,4,6-trimethylphenyl)imidazolium bromide, [IMesH][Br] and 1,3-bis(2,4,6-trimethylphenyl)-2-bromoimidazolium bromide, [IMesBr][Br]. Treatment of IMes with 2.0 equiv. of carbon tetrabromide, CBr4, in tetrahydrofuran or benzene yields the new NHC 1,3-bis(2,4,6-trimethylphenyl)-4,5-dibromoimidazol-2-ylidene, IMesBr2. IMesBr2 is indefinitely stable in air and has been characterised by XRD. The molecular and supramolecular structures of compounds [IMesBr][Br]·3MeCN, [IMesH][Br], [IMesCl][Cl]·MeCN and [IMesCl][AlCl4], the latter formed from the addition of aluminium trichloride to [IMesCl][Cl], are discussed.

Graphical abstract: Studies of the reactivity of N-heterocyclic carbenes with halogen and halide sources

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Publication details

The article was received on 08 May 2002, accepted on 06 Aug 2002 and first published on 09 Sep 2002


Article type: Paper
DOI: 10.1039/B204422F
Citation: New J. Chem., 2002,26, 1296-1303
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    Studies of the reactivity of N-heterocyclic carbenes with halogen and halide sources

    M. L. Cole, C. Jones and P. C. Junk, New J. Chem., 2002, 26, 1296
    DOI: 10.1039/B204422F

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