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Reactivity of 1,3-dimethylimidazolium-2-carboxylate with dimethylcarbonate at high temperature: Unexpected 2-ethyl-functionalisation of the imidazolium moiety and employment of the NHC-CO2/dimethylcarbonate system in a base promoted reaction

Paper ID Volume ID Publish Year Pages File Format Full-Text
50163 46783 2014 4 PDF Available
Title
Reactivity of 1,3-dimethylimidazolium-2-carboxylate with dimethylcarbonate at high temperature: Unexpected 2-ethyl-functionalisation of the imidazolium moiety and employment of the NHC-CO2/dimethylcarbonate system in a base promoted reaction
Abstract

•Reactivity of 1,3-dimethylimidazolium-2-carboxylate with dimethylcarbonate•Unexpected 2-ethyl-functionalization of the imidazolium moiety•Synthesis and characterization of 2-ethyl-1,3-dimethylimidazolium methyl carbonate•Synthesis and characterization of 2-ethyl-1,3-dimethylimidazolium-4-carboxylate•Synthesis of 1,7-heptanedioic acid dimethyl ester

The reaction of 1,3-dimethylimidazolium-2-carboxylate and dimethylcarbonate (DMC) at high temperature yielded the new compounds 2-ethyl-1,3-dimethylimidazolium methyl carbonate salt and 2-ethyl-1,3-dimethylimidazolium-4-carboxylate zwitterion which were obtained as a mixture in approximately 4:1 molar ratio. The compounds were also isolated in pure form through alternative synthetic procedures and characterized by ESI-HRMS, 1H, 13C NMR and FTIR spectroscopy. The 1,3-dimethylimidazolium-2-carboxylate/dimethylcarbonate system was employed in the synthesis of 1,7-heptanedioic acid dimethyl ester from cyclohexanone and DMC. The target compound was obtained in 49% yield and 66% selectivity.

Graphical abstractReactivity of 1,3-dimethylimidazolium-2-carboxylate with dimethylcarbonate at high temperature: unexpected 2-ethyl-functionalisation of the imidazolium moiety and employment of the NHC-CO2/dimethylcarbonate system in a base promoted reaction.Figure optionsDownload full-size imageDownload as PowerPoint slide

Keywords
1,3-Dimethylimidazolium-2-carboxylate; Dimethylcarbonate; N-heterocyclic carbenes; 2-Ethyl-1,3-dimethylimidazolium methyl carbonate salt
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Reactivity of 1,3-dimethylimidazolium-2-carboxylate with dimethylcarbonate at high temperature: Unexpected 2-ethyl-functionalisation of the imidazolium moiety and employment of the NHC-CO2/dimethylcarbonate system in a base promoted reaction
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Publisher
Database: Elsevier - ScienceDirect
Journal: Catalysis Communications - Volume 46, 10 February 2014, Pages 94–97
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us