1: With bis(tricyclohexylphosphine)benzylidene ruthenium(IV) dichloride in toluene T=25°C; 2: With bis(tricyclohexylphosphine)benzylidene ruthenium(IV) dichloride; ethyl vinyl ether in toluene T=25 - 110°C;

1.1: NaH / tetrahydrofuran / 0.5 h / Heating 1.2: 81 percent / tetrahydrofuran / Heating 2.1: [Cl2(PCy3)2Ru=CHPh] / toluene / 25 °C 2.2: 74 percent / EtOCH=CH2; [Cl2(PCy3)2Ru=CHPh] / toluene / 25 - 110 °C View Scheme

1.1: 76 percent / diethyl ether; tetrahydrofuran / 0.5 h / 0 °C 2.1: NaH / tetrahydrofuran / 0.5 h / Heating 2.2: 81 percent / tetrahydrofuran / Heating 3.1: [Cl2(PCy3)2Ru=CHPh] / toluene / 25 °C 3.2: 74 percent / EtOCH=CH2; [Cl2(PCy3)2Ru=CHPh] / toluene / 25 - 110 °C View Scheme