1: With ozone in dichloromethane T=-78°C; 1 h; 2: With dimethylsulfide in dichloromethane T=-78 - 25°C; 3: With triphenylphosphine in dichloromethane T=25°C; 5 h; Further stages.;

Oxone® in water; acetone T=20°C; 0.0333333 h; Cooling with ice;

1.1: 99 percent / LiCl / [Pd(PPh3)4] / tetrahydrofuran / 48 h / Heating 2.1: ozone / CH2Cl2 / 1 h / -78 °C 2.2: Me2S / CH2Cl2 / -78 - 25 °C 2.3: 94 percent / PPh3 / CH2Cl2 / 5 h / 25 °C View Scheme

1: 4-(N,N-dimethlyamino)pyridine; thionyl chloride / ethylene glycol dimethyl ether / 24 h / 0 - 20 °C / |Inert atmosphere 2: pyridine / dichloromethane / 1 h / 0 °C 3: lithium chloride; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 48 h / |Reflux 4: 4-methylmorpholine N-oxide; osmium(VIII) oxide / acetone; water / 4 h / 20 °C 5: sodium periodate; sodium hydrogencarbonate / tetrahydrofuran; water / 0.5 h / 0 - 20 °C View Scheme

1: pyridine / dichloromethane / 1 h / 0 °C 2: lithium chloride; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 48 h / |Reflux 3: 4-methylmorpholine N-oxide; osmium(VIII) oxide / acetone; water / 4 h / 20 °C 4: sodium periodate; sodium hydrogencarbonate / tetrahydrofuran; water / 0.5 h / 0 - 20 °C View Scheme