periodic acid in water T=40°C; 4 h;

pyridine; dimethylsulfide; ozone 1.) CH2Cl2, -78 deg C, 4.5 h, 2.) CH2Cl2, room temp., 5 h; Yield givenMultistep reaction;

1: 1.) NaH / 1.) dimethoxyethane, room temperature, 2 h, 2.) room temperature, 40 h 2: 100 percent / m-chloroperbenzoic acid / CH2Cl2 / 1 h / Ambient temperature 3: 89 percent / periodic acid / H2O / 4 h / 40 °C View Scheme

1: 1.) NaH / 1.) dimethoxyethane, room temperature, 2 h, 2.) room temperature, 40 h 2: 100 percent / m-chloroperbenzoic acid / CH2Cl2 / 1 h / Ambient temperature 3: 89 percent / periodic acid / H2O / 4 h / 40 °C View Scheme