1: With ozone in ethyl acetate T=-78°C; 2: With hydrogen; palladium on activated charcoal in ethyl acetate T=20°C; P=1551.44 Torr; 0.0833333 h;

1.1: sodium hydride / tetrahydrofuran / 0 - 20 °C 1.2: 94.8 percent / tetrahydrofuran / 120 h / Heating 2.1: 99.6 percent / bis(tricyclohexylphosphine)benzylidine ruthenium dichloride / CH2Cl2 / 2 h 3.1: ozone / ethyl acetate / -78 °C 3.2: H2 / Pd/C / ethyl acetate / 0.08 h / 20 °C / 1551.44 Torr View Scheme

1.1: 99.6 percent / bis(tricyclohexylphosphine)benzylidine ruthenium dichloride / CH2Cl2 / 2 h 2.1: ozone / ethyl acetate / -78 °C 2.2: H2 / Pd/C / ethyl acetate / 0.08 h / 20 °C / 1551.44 Torr View Scheme

1.1: 76.3 percent / triphenylphosphine; imidazole; iodine / CH2Cl2 / 6 h / 20 °C 2.1: sodium hydride / tetrahydrofuran / 0 - 20 °C 2.2: 94.8 percent / tetrahydrofuran / 120 h / Heating 3.1: 99.6 percent / bis(tricyclohexylphosphine)benzylidine ruthenium dichloride / CH2Cl2 / 2 h 4.1: ozone / ethyl acetate / -78 °C 4.2: H2 / Pd/C / ethyl acetate / 0.08 h / 20 °C / 1551.44 Torr View Scheme