The Ru(η6-naphthalene)(η4-cycloocta-1,5-diene)/ Acetonitrile System in the Selective Dimerization of Methyl Acrylate to trans-Dimethyl-2-hexenedioate

Abstract

The complex Ru(η6-naphthalene)(η4-cycloocta-1,5-diene), I, in the presence of acetonitrile, selectively catalyzes the tail-to-tail dimerization of methyl acrylate to trans-dimethyl-2-hexenedioate at 140 °C. An examination of the stoichiometric reaction between I and methyl acrylate shows that acetonitrile promotes removal of the dimer from the coordination sphere of ruthenium. Using tetrahydrofuran or N-methyl-2-pyrrolidinone as solvents, a long-lived catalyst is obtained which can be re-used without appreciable loss of activity. Show more