Stepwise catalytic transformations of renewable feedstock arising from plant oils

Authors

  • Antoine Dupé,

    1. UMR 6226 CNRS-Université de Rennes 1, Institut des Sciences Chimiques de Rennes, Organométalliques, Matériaux et Catalyse, Centre of Catalysis and Green Chemistry, Campus de Beaulieu, Rennes, Cedex, France
    2. ADEME, Angers Cedex, France
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  • Virginie Le Ravalec,

    1. UMR 6226 CNRS-Université de Rennes 1, Institut des Sciences Chimiques de Rennes, Organométalliques, Matériaux et Catalyse, Centre of Catalysis and Green Chemistry, Campus de Beaulieu, Rennes, Cedex, France
    2. ADEME, Angers Cedex, France
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  • Cédric Fischmeister,

    1. UMR 6226 CNRS-Université de Rennes 1, Institut des Sciences Chimiques de Rennes, Organométalliques, Matériaux et Catalyse, Centre of Catalysis and Green Chemistry, Campus de Beaulieu, Rennes, Cedex, France
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  • Christian Bruneau

    Corresponding author
    • UMR 6226 CNRS-Université de Rennes 1, Institut des Sciences Chimiques de Rennes, Organométalliques, Matériaux et Catalyse, Centre of Catalysis and Green Chemistry, Campus de Beaulieu, Rennes, Cedex, France
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Correspondence: Dr. Christian Bruneau, UMR 6226 CNRS-Université de Rennes 1, Institut des Sciences Chimiques de Rennes, Organométalliques, Matériaux et Catalyse, Centre of Catalysis and Green Chemistry, 263, Avenue du général Leclerc, Campus de Beaulieu, 35042 Rennes Cedex, France

E-mail: christian.bruneau@univ-rennes1.fr

Fax: +33 2 23236939

Abstract

Two synthetic approaches to produce functionalized plant oil derivatives were investigated. The ruthenium-catalyzed ene-yne cross-metathesis of propargylic carbonates with terminal olefins arising from ethenolysis of methyl oleate provides conjugated dienes. It was shown that the reactivity of these dienes in Diels–Alder [4 + 2]-cycloaddition with symmetrical electron-deficient alkynes towards the formation of cyclohexadienes was effective but limited by stereochemical considerations. On the other hand, the stepwise ene-yne cross-metathesis followed by ruthenium-catalyzed nucleophilic allylic substitution by O, N, and C-nucleophiles was very efficient both in term of reactivity and regioselectivity.

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