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Ruthenium Carbene Mediated Metathesis of Oleate-Type Fatty Compounds
Department of Chemistry, North-West University, P/Bag X2046, Mafikeng, 2735, South Africa
School of Chemistry, North-West University, P/Bag X6001, Potchefstroom, South Africa
* Author to whom correspondence should be addressed.
Received: 16 November 2007; in revised form: 28 March 2008 / Accepted: 17 April 2008 / Published: 18 April 2008
Abstract: 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
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MDPI and ACS Style
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.
Marvey BB, Segakweng CK, Vosloo MHC. Ruthenium Carbene Mediated Metathesis of Oleate-Type Fatty Compounds. International Journal of Molecular Sciences. 2008; 9(4):615-625.
Marvey, Bassie B.; Segakweng, Constance K.; Vosloo, Manie H.C. 2008. "Ruthenium Carbene Mediated Metathesis of Oleate-Type Fatty Compounds." Int. J. Mol. Sci. 9, no. 4: 615-625.