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Issue 9, 2011
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A green route to nitrogen-containing groups: the acrylonitrile cross-metathesis and applications to plant oil derivatives

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Abstract

Acrylonitrile has become a renewable material arising from glycerol. It can now be used as an available key product to introduce a nitrogen-containing functionality into a molecule by cross-metathesis. This review successively presents the developments of catalytic cross-metathesis of acrylonitrile with functional alkenes: (i) the first steps of cross-metathesis of acrylonitrile with simple terminal alkenes, of which the successes were linked to the progressive discoveries of efficient alkene metathesis catalysts, (ii) some contributions of this catalytic reaction to synthesis of complex molecules and (iii) the access to renewable α,ω-bifunctional compounds by acrylonitrile cross-metathesis with fatty acid derivatives, arising from plant oils. The combination of the renewable acrylonitrile and fatty acid derivatives, by catalysis under mild conditions with only ethylene as a by-product, constitutes a clear contribution to green chemistry for the production of useful intermediates.

Graphical abstract: A green route to nitrogen-containing groups: the acrylonitrile cross-metathesis and applications to plant oil derivatives

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Publication details

The article was received on 07 Apr 2011, accepted on 13 May 2011 and first published on 04 Jul 2011


Article type: Critical Review
DOI: 10.1039/C1GC15377C
Citation: Green Chem., 2011,13, 2258-2271
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    A green route to nitrogen-containing groups: the acrylonitrile cross-metathesis and applications to plant oil derivatives

    X. Miao, P. H. Dixneuf, C. Fischmeister and C. Bruneau, Green Chem., 2011, 13, 2258
    DOI: 10.1039/C1GC15377C

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