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Molecules 2009, 14(6), 2235-2245; doi:10.3390/molecules14062235

A Facile Route to C2-Substituted Imidazolium Ionic Liquids

 and *
Department of Chemistry, Middle Tennessee State University, Murfreesboro, TN 37132, USA
* Author to whom correspondence should be addressed.
Received: 14 May 2009 / Revised: 10 June 2009 / Accepted: 16 June 2009 / Published: 19 June 2009
(This article belongs to the Special Issue Ionic Liquids)
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A convenient route for the preparation of C2-substituted imidazolium ionic liquids is reported. This method involves the alkylation of N-heterocyclic carbenes, which are readily generated from the C2-unsubstituted imidazolium ionic liquids. It works well for non-functionalized alkyl chlorides, and less well for alkyl bromides and iodides, likely due to competing elimination reactions. The resulting C2-substituted salts can be transformed into ionic liquids via standard anion metathesis reactions.
Keywords: ionic liquids; N-heterocyclic carbenes; alkylation; imidazolium cation; substitution ionic liquids; N-heterocyclic carbenes; alkylation; imidazolium cation; substitution
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Ennis, E.; Handy, S.T. A Facile Route to C2-Substituted Imidazolium Ionic Liquids. Molecules 2009, 14, 2235-2245.

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