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Issue 3, 2010
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Diels–Alder reaction of vinylene carbonate and 2,5-dimethylfuran: kinetic vs. thermodynamic control

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Abstract

The Diels–Alder reaction between 2,5-dimethylfuran and vinylene carbonate was studied, both from an experimental and a theoretical point of view. The system was shown to slowly reach a thermodynamic equilibrium, characterized by the almost exclusive formation of the exo isomer. We rationalized these results by a comparison with classical systems involving maleic anhydride, and highlighted the different reactivity of vinylene carbonate as a dienophile. Finally, a preparative scale synthesis of pure exo isomer 4, a potentially useful synthon, ensued from this work.

Graphical abstract: Diels–Alder reaction of vinylene carbonate and 2,5-dimethylfuran: kinetic vs. thermodynamic control

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Publication details

The article was received on 06 Oct 2009, accepted on 13 Nov 2009 and first published on 19 Jan 2010


Article type: Paper
DOI: 10.1039/B9NJ00536F
Citation: New J. Chem., 2010,34, 517-525

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    Diels–Alder reaction of vinylene carbonate and 2,5-dimethylfuran: kinetic vs. thermodynamic control

    C. Taffin, G. Kreutler, D. Bourgeois, E. Clot and C. Périgaud, New J. Chem., 2010, 34, 517
    DOI: 10.1039/B9NJ00536F

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