Cross metathesis of bio-sourced fatty nitriles with acrylonitrile

We report the cross metathesis of two olefinic partners containing different types of nitrile functionality. Thus, cross metathesis of fatty nitriles with acrylonitrile have been achieved with olefin metathesis ruthenium catalysts. 10-Undecenenitrile provides 2-dodecenedinitrile with a high turnover...

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Bibliographic Details
Published inMonatshefte für Chemie Vol. 146; no. 7; pp. 1107 - 1113
Main Authors Bidange, Johan, Fischmeister, Cédric, Bruneau, Christian, Dubois, Jean-Luc, Couturier, Jean-Luc
Format Journal Article
LanguageEnglish
Published Vienna Springer Vienna 01.07.2015
Springer Verlag
Subjects
Analytical Chemistry
Chemical Sciences
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Inorganic Chemistry
Organic Chemistry
Original Paper
Physical Chemistry
Theoretical and Computational Chemistry
Green chemistry
α,ω-Dinitriles
Homogeneous catalysis
Ruthenium catalysis
Renewables
ω-Dinitriles
α
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Summary:We report the cross metathesis of two olefinic partners containing different types of nitrile functionality. Thus, cross metathesis of fatty nitriles with acrylonitrile have been achieved with olefin metathesis ruthenium catalysts. 10-Undecenenitrile provides 2-dodecenedinitrile with a high turnover number of 13,280 in the green solvent, diethyl carbonate. Cross metathesis with the internal carbon–carbon double bond of oleonitrile gave the expected products, and the cleavage of the internal double bond proved to be more difficult probably owing to faster catalyst decomposition. Graphical abstract
ISSN:0026-9247
1434-4475
DOI:10.1007/s00706-015-1480-1