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2,2,4,4,6,6,8,8-Octamethyl-1,5-dioxo-2,4,6,8-tetrasila-3,7-exo-dimethylenecyclooctane (1) (whose X-ray structure has been determined) is a good model to study the reactivity of an exocyclic vinyl bond at silicon with styrene occurring in the presence of RuHCl(CO)(PPh3)3 (I). Two products are formed initially:  the linear 2 by ring opening of 1 and the cyclic 3 by condensation with evolution of ethylene. In the presence of an excess of styrene, 2 undergoes consecutive reactions giving subsequent styryl derivatives. Effective catalysis by I and the lack of activity of Ru−carbenes (II) for the reaction were examined. An MS study of the products (2 D and 3 D ) of the reaction of deuterated styrene with 1 provides convincing evidence for a mechanism that does not involve a metallacarbene. A sequential insertion−elimination mechanism is proposed for the catalytic process.

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