Studies of the reactivity of N-heterocyclic carbenes with halogen and halide sources
Date
2002
Authors
Cole, Marcus Lawford
Jones, Cameron
Junk, Peter C.
Editors
Advisors
Journal Title
Journal ISSN
Volume Title
Type:
Journal article
Citation
New Journal of Chemistry, 2002; 26 (10):1296-1303
Statement of Responsibility
Marcus L. Cole, Cameron Jones and Peter C. Junk
Conference Name
DOI
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.
School/Discipline
School of Chemistry and Physics
Dissertation Note
Provenance
Description
© Royal Society of Chemistry 2002