Ruthenium carbene mediated metathesis of oleate-type fatty compounds.
The complexes RuCl(2)(PCy(3))(2)(=CHPh), 1, and RuCl(2)(PCy(3))(H(2)IMes)(=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.
Marvey
Bassie B
BB
Department of Chemistry, North-West University, P/Bag X2046, Mafikeng, 2735, South Africa.
Segakweng
Constance K
CK
Department of Chemistry, North-West University, P/Bag X2046, Mafikeng, 2735, South Africa.
Vosloo
Manie H C
MHC
0000-0002-5879-323X
School of Chemistry, North-West University, P/Bag X6001, Potchefstroom, South Africa.