ammonium cerium(IV) nitrate in water; acetonitrile T=0 - 2°C; 0.666667 h;

1: 90 percent / 70percent perchloric acid, hydrogen / 5percent palladium-charcoal / acetic acid / 1.5 h / 70 °C 2: triethylamine / CH2Cl2 / 1 h / -5 °C 3: sodium iodide / acetone / 2 h / 50 °C 4: 1.) sodium amide, 2.) hexamethylphosphoramide / 1.) THF, 50 deg C, 1.5 h, 2.) room temperature, 1 h 5: toluene-p-sulphonic acid / methanol / 0.5 h / 70 °C 6: triethylamine / CH2Cl2 / 1 h / -5 °C 7: sodium iodide / acetone / 2 h / 50 °C 8: 1.) sodium amide / 1.) Et2O, liquid ammonia, -50 deg C - -40 deg C, 60 min, 2.) -50 deg C - -40 deg C, 100 min 9: toluene-p-sulphonic acid / methanol / 0.5 h / 70 °C 10: 91 percent / cerium(IV) ammonium nitrate / acetonitrile; H2O / 0.67 h / 0 - 2 °C View Scheme

1: triethylamine / CH2Cl2 / 1 h / -5 °C 2: sodium iodide / acetone / 2 h / 50 °C 3: 1.) sodium amide, 2.) hexamethylphosphoramide / 1.) THF, 50 deg C, 1.5 h, 2.) room temperature, 1 h 4: toluene-p-sulphonic acid / methanol / 0.5 h / 70 °C 5: triethylamine / CH2Cl2 / 1 h / -5 °C 6: sodium iodide / acetone / 2 h / 50 °C 7: 1.) sodium amide / 1.) Et2O, liquid ammonia, -50 deg C - -40 deg C, 60 min, 2.) -50 deg C - -40 deg C, 100 min 8: toluene-p-sulphonic acid / methanol / 0.5 h / 70 °C 9: 91 percent / cerium(IV) ammonium nitrate / acetonitrile; H2O / 0.67 h / 0 - 2 °C View Scheme

1: 1.) sodium amide, 2.) hexamethylphosphoramide / 1.) THF, 50 deg C, 1.5 h, 2.) room temperature, 1 h 2: toluene-p-sulphonic acid / methanol / 0.5 h / 70 °C 3: triethylamine / CH2Cl2 / 1 h / -5 °C 4: sodium iodide / acetone / 2 h / 50 °C 5: 1.) sodium amide / 1.) Et2O, liquid ammonia, -50 deg C - -40 deg C, 60 min, 2.) -50 deg C - -40 deg C, 100 min 6: toluene-p-sulphonic acid / methanol / 0.5 h / 70 °C 7: 91 percent / cerium(IV) ammonium nitrate / acetonitrile; H2O / 0.67 h / 0 - 2 °C View Scheme

1: 1.) sodium amide, 2.) hexamethylphosphoramide / 1.) THF, 50 deg C, 1.5 h, 2.) room temperature, 1 h 2: toluene-p-sulphonic acid / methanol / 0.5 h / 70 °C 3: triethylamine / CH2Cl2 / 1 h / -5 °C 4: sodium iodide / acetone / 2 h / 50 °C 5: 1.) sodium amide / 1.) Et2O, liquid ammonia, -50 deg C - -40 deg C, 60 min, 2.) -50 deg C - -40 deg C, 100 min 6: toluene-p-sulphonic acid / methanol / 0.5 h / 70 °C 7: 91 percent / cerium(IV) ammonium nitrate / acetonitrile; H2O / 0.67 h / 0 - 2 °C View Scheme

1: 1.) sodium amide, 2.) hexamethylphosphoramide / 1.) THF, 50 deg C, 1.5 h, 2.) room temperature, 1 h 2: toluene-p-sulphonic acid / methanol / 0.5 h / 70 °C 3: 91 percent / cerium(IV) ammonium nitrate / acetonitrile; H2O / 0.67 h / 0 - 2 °C View Scheme

1: 1.) sodium amide / 1.) Et2O, liquid ammonia, -50 deg C - -40 deg C, 60 min, 2.) -50 deg C - -40 deg C, 100 min 2: toluene-p-sulphonic acid / methanol / 0.5 h / 70 °C 3: 91 percent / cerium(IV) ammonium nitrate / acetonitrile; H2O / 0.67 h / 0 - 2 °C View Scheme

1: triethylamine / CH2Cl2 / 1 h / -5 °C 2: sodium iodide / acetone / 2 h / 50 °C 3: 1.) sodium amide / 1.) Et2O, liquid ammonia, -50 deg C - -40 deg C, 60 min, 2.) -50 deg C - -40 deg C, 100 min 4: toluene-p-sulphonic acid / methanol / 0.5 h / 70 °C 5: 91 percent / cerium(IV) ammonium nitrate / acetonitrile; H2O / 0.67 h / 0 - 2 °C View Scheme

1: toluene-p-sulphonic acid / methanol / 0.5 h / 70 °C 2: 91 percent / cerium(IV) ammonium nitrate / acetonitrile; H2O / 0.67 h / 0 - 2 °C View Scheme