The benzylidene complexes [Cl 2 (PCy 3 ) 2 RudC(C 6 H 4 R-p)H] [R ) H (1a), Cl (1b), OMe (1c)] react with (E)-bis(trimethylsilyl)ethene (2) to give 3,3-bis(trimethylsilylAnalogously, reaction of 1a with trimethylsilylstilbene gives H(Ph)CdC(SiMe 3 )H (4a). In contrast, reaction of 1a with para-methoxysubstituted trimethylsilylstilbene, H(Me 3 Si)CdC(C 6 H 4 OMe-p)H (4b), affords mixtures of the crossmetathesis product, H(Me 3 Si)CdC(Ph)H, and various propene derivatives. Labeling experiments have been carried out. The mechanism of these reactions is discussed.