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Type: Journal article
Title: Studies of the reactivity of N-heterocyclic carbenes with halogen and halide sources
Author: Cole, Marcus Lawford
Jones, Cameron
Junk, Peter C.
Citation: New Journal of Chemistry, 2002; 26 (10):1296-1303
Publisher: Royal Society Chemistry
Issue Date: 2002
ISSN: 1144-0546
School/Discipline: School of Chemistry and Physics
Statement of
Marcus L. Cole, Cameron Jones and Peter C. Junk
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.
Description: © Royal Society of Chemistry 2002
RMID: 0020064526
DOI: 10.1039/b204422f
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Appears in Collections:Chemistry publications

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