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Int. J. Mol. Sci. 2008, 9(4), 615-625; doi:10.3390/ijms9040615

Ruthenium Carbene Mediated Metathesis of Oleate-Type Fatty Compounds

1,* , 1
Received: 16 November 2007 / Revised: 28 March 2008 / Accepted: 17 April 2008 / Published: 18 April 2008
(This article belongs to the Section Green Chemistry)
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The complexes RuCl2(PCy3)2(=CHPh), 1, and RuCl2(PCy3)(H2IMes)(=CHPh), 2, proved to be active catalysts for the self-metathesis of oleate-type fatty compounds containing the ester, hydroxyl, epoxy and carboxylic acid functional groups. At elevated reaction temperatures 2 showed a higher activity, stability and lower selectivity for primary metathesis products compared to 1. A profound influence of organic functional groups on catalyst activity and selectivity was found and from relative activities and selectivities 2 has proved to be more resistant to deactivation by polar functional groups and more inclined to promote double bond isomerisation than 1. The observed catalyst deactivation by oxygen-containing functional groups could be attributed to a phosphine displacement side reaction.
Keywords: Olefin Metathesis; Grubbs catalysts; oleate-type fatty compounds Olefin Metathesis; Grubbs catalysts; oleate-type fatty compounds
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Marvey, B.B.; Segakweng, C.K.; Vosloo, M.H.C. Ruthenium Carbene Mediated Metathesis of Oleate-Type Fatty Compounds. Int. J. Mol. Sci. 2008, 9, 615-625.

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