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

被引:66
作者
Cole, ML
Jones, C
Junk, PC
机构
[1] Cardiff Univ, Dept Chem, Cardiff CF10 3TB, S Glam, Wales
[2] Monash Univ, Sch Chem, Clayton, Vic 3800, Australia
关键词
D O I
10.1039/b204422f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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, IMesBr(2). IMesBr(2) 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.
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页码:1296 / 1303
页数:8
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