ozone in dichloromethane T=0°C; 2 h;

KNO2; acetic anhydride; dimethyl sulfoxide in N,N,N',N',N'',N''-hexamethylphosphoric triamide 0.5 h; Ambient temperature;

1: 1.) N-chlorosuccinimide, 2.) sodium methoxide / 1.) a) methylene chloride, - 20 deg C, 1 h, b) RT, 1 h, 2.) methanol, 10 min. 2: m-chloroperbenzoic acid / CH2Cl2 / 0.5 h / 0 °C 3: 36 percent / O3 / CH2Cl2 / 2 h / 0 °C View Scheme

1: m-chloroperbenzoic acid / CH2Cl2 / 0.5 h / 0 °C 2: 36 percent / O3 / CH2Cl2 / 2 h / 0 °C View Scheme

hydrogenchloride; hydrogen; palladium in methanol; hexane; ethyl acetate

potassium permanganate; ammonia T=-33°C; 6 h;