1: 70 percent / ozone, methanolic NaOH / CH2Cl2 / -70 °C 2: 82 percent / NaBH4, Na2HPO4*12H2O / methanol / 1.) 0 deg C, 5 min, 2.) RT, 24 h View Scheme

dimethylsulfide; ozone 1.) CH2Cl2, -60 deg C, 2.) -60 deg C, then room temp.; Yield given. Multistep reaction;

1: 1.) O3, 2.) Me2S / 1.) CH2Cl2, -60 deg C, 2.) -60 deg C, then room temp. 2: 89 percent / 1percent aq. NaOH / diethyl ether / 72 h / Ambient temperature View Scheme