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Molecules 2009, 14(6), 2235-2245;

A Facile Route to C2-Substituted Imidazolium Ionic Liquids

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 Collection 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

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This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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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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