1: With ozone in dichloromethane T=-78°C; 2: With triphenylphosphine in dichloromethane T=-78°C; 0.166667 h;

1.1: 97 percent / LiAlH4 / diethyl ether / 1.33 h / -78 - 0 °C 2.1: 67 percent / Et3N; SO3*py / CH2Cl2; dimethylsulfoxide / 1 h 3.1: O3 / CH2Cl2 / -78 °C 3.2: PPh3 / CH2Cl2 / 0.17 h / -78 °C View Scheme

1.1: 67 percent / Et3N; SO3*py / CH2Cl2; dimethylsulfoxide / 1 h 2.1: O3 / CH2Cl2 / -78 °C 2.2: PPh3 / CH2Cl2 / 0.17 h / -78 °C View Scheme

sodium periodate

(hydrolysis);