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Molbank 2018, 2018(1), M974;

3-[2-(Oxiran-2-yl)ethyl]-1-{4-[(2-oxiran-2-yl)ethoxy]benzyl}imidazolium bis(Trifluoromethane)sulfonimide

Laboratory of Molecular and Thio-organic Chemistry, ENSICAEN, Normandy University, CNRS, 6 boulevard du Maréchal Juin, 14050 Caen, France
Lyon University, INSA Lyon, UMR CNRS 5223, IMP Polymer Materials Engineering, F-69621 Villeurbanne, France
Authors to whom correspondence should be addressed.
Received: 19 December 2017 / Revised: 9 January 2018 / Accepted: 10 January 2018 / Published: 13 January 2018
(This article belongs to the Special Issue Heterocycles)
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The synthesis of 3-[2-(oxiran-2-yl)ethyl]-1-{4-[(2-oxiran-2-yl)ethoxy]benzyl}imidazolium bis(trifluoromethane)sulfonimide was achieved in seven steps with an overall yield of 63%. This ionic liquid monomer is based on an imidazolium core containing a phenoxy moiety and aliphatic chains with a reactive epoxide at both ends. This imidazolium was obtained by an efficient, reproducible, and scalable synthesis from inexpensive reagents. In the last step, a powerful oxidative agent was successfully used to generate two epoxy functions with only acetone as a byproduct. The monomer structure and intermediates were analyzed by NMR experiments, infrared, and mass spectra. In addition, the thermal properties of the diepoxide were evaluated by thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). View Full-Text
Keywords: epoxides; imidazolium; ionic liquid; monomer epoxides; imidazolium; ionic liquid; monomer

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Chardin, C.; Rouden, J.; Livi, S.; Baudoux, J. 3-[2-(Oxiran-2-yl)ethyl]-1-{4-[(2-oxiran-2-yl)ethoxy]benzyl}imidazolium bis(Trifluoromethane)sulfonimide. Molbank 2018, 2018, M974.

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