Collect. Czech. Chem. Commun. 1984, 49, 1736-1745

Metathesis of methyl 10-undecenoate

Hynek Balcar, Alena Dosedlová, Vladimír Hanuš, Lidmila Petrusová and Bohumír Matyska

J. Heyrovský Institute of Physical Chemistry and Electrochemistry, Czechoslovak Academy of Sciences, 121 38 Prague 2


The metathesis of methyl 10-undecenoate was studied using the WCl6 + (CH3)4Sn catalyst system. The rate of metathesis and the maximum degree of conversion are affected markedly by the reactions of the ester, and of the other oxygen compounds if present, with tungsten hexachloride. Introduction of an oxygen ligand to the central tungsten atom of the active centre increases the reactivity and stability of the latter, thus affecting positively the initial rate of the metathesis reaction. At the same time, however, the rate of the catalyst deactivation increasing concentration of the ester, whereupon the degree of the conversion decreases. As a result of competition of the two effects, a maximum appears in the dependence of the amount of the ester reacted on the ester-to-tungsten hexachloride ratio.