ammonia

ammonium cerium(IV) nitrate in water; acetonitrile 1 h; Ambient temperature;

1: 1.) MgSO4, 2.) N,N-diethylaniline / 1.) Et2O, 2 h, RT, 2.) toluene, -78 deg C to RT, 24 h 2: N-chlorosuccinimide / 40 deg C, 2 h; 80 deg C, 1 h 3: SiO2, H2O / 1.) 35 deg C, overnight then 60 deg C, 30 min, 2.) benzene, 1 h 4: 58 percent / Raney nickel (W-2) / ethanol / 3 h / Heating 5: 56 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature 6: 47 percent / cerium(IV) ammonium nitrate / acetonitrile; H2O / 1 h / Ambient temperature View Scheme

1: 56 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature 2: 47 percent / cerium(IV) ammonium nitrate / acetonitrile; H2O / 1 h / Ambient temperature View Scheme

1: 58 percent / Raney nickel (W-2) / ethanol / 3 h / Heating 2: 56 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature 3: 47 percent / cerium(IV) ammonium nitrate / acetonitrile; H2O / 1 h / Ambient temperature View Scheme

1: SiO2, H2O / 1.) 35 deg C, overnight then 60 deg C, 30 min, 2.) benzene, 1 h 2: 58 percent / Raney nickel (W-2) / ethanol / 3 h / Heating 3: 56 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature 4: 47 percent / cerium(IV) ammonium nitrate / acetonitrile; H2O / 1 h / Ambient temperature View Scheme