Toward a simulation approach for alkene ring-closing metathesis: Scope and limitations of a model for RCM

A published model for revealing solvent effects on the ring-closing metathesis (RCM) reaction of diethyl diallylmalonate 7 has been evaluated over a wider range of conditions, to assess its suitability for new applications. Unfortunately, the model is too flexible and the published rate constants do not agree with experimental studies in the literature. However, by fixing the values of important rate constants and restricting the concentration ranges studied, useful conclusions can be drawn about the relative rates of RCM of different substrates, precatalyst concentration can be simulated accurately and the effect of precatalyst loading can be anticipated. Progress has also been made toward applying the model to precatalyst evaluation, but further modifications to the model are necessary to achieve much broader aims. © 2011 American Chemical Society.