Collect. Czech. Chem. Commun. 1989, 54, 455-461

Cometathesis of methyl oleate with α-olefins

Bohumír Matyska, Alena Dosedlová, Lidmila Petrusová and Hynek Balcar

The J. Heyrovský Institute of Physical Chemistry and Electrochemistry, Czechoslovak Academy of Sciences, 182 23 Prague 8


Cometathesis of methyl oleate with 1-hexene or with other α-olefins affords two new esters and two new olefins. In the case of 1-hexene these products are methyl 9-decenoate, methyl 9-tetradecenoate, 1-decene and 5-tetradecene. At the same time, the formation of the esters and olefins with shorter chains(i.e. decene and decenoate) is distinctly preffered. Obviously, the transfer of methylene group from the alkene to the ester molecule is much easier than that of the alkylidene moiety. The non-stoichiometric course of cometathesis is associated with the carbene mechanism of the reaction.