ammonium cerium(IV) nitrate in water; acetonitrile 1.) -7 deg C, 1 h, 2.) room temp., 2 h;

potassium hydroxide in tetrahydrofuran; methanol; water T=20°C; 1 h;

1: 1.) HMPA, n-BuLi / 1.) THF, hexane, -40 deg C, 30 min, then -40 to -10 deg C, 1 h, -10 deg C, 1h, 2.) THF, hexane, overnight 2: 1.) ammonium cerium(IV) nitrate, 2.) HClO4 / 1.) CH3CN, H2O, -7 deg C, 1 h, then room temp., 2 h, 2.) CH2Cl2, room temp., 4 h View Scheme

1: mCPBA / 2 h / Ambient temperature 2: aq. KOH / ethanol / 2 h / 50 °C 3: 94 percent / NaH / dimethylformamide / 1 h / Ambient temperature 4: 1.) HMPA, n-BuLi / 1.) THF, hexane, -40 deg C, 30 min, then -40 to -10 deg C, 1 h, -10 deg C, 1h, 2.) THF, hexane, overnight 5: 1.) ammonium cerium(IV) nitrate, 2.) HClO4 / 1.) CH3CN, H2O, -7 deg C, 1 h, then room temp., 2 h, 2.) CH2Cl2, room temp., 4 h View Scheme

1: 94 percent / NaH / dimethylformamide / 1 h / Ambient temperature 2: 1.) HMPA, n-BuLi / 1.) THF, hexane, -40 deg C, 30 min, then -40 to -10 deg C, 1 h, -10 deg C, 1h, 2.) THF, hexane, overnight 3: 1.) ammonium cerium(IV) nitrate, 2.) HClO4 / 1.) CH3CN, H2O, -7 deg C, 1 h, then room temp., 2 h, 2.) CH2Cl2, room temp., 4 h View Scheme

perchloric acid; ammonium cerium(IV) nitrate 1.) CH3CN, H2O, -7 deg C, 1 h, then room temp., 2 h, 2.) CH2Cl2, room temp., 4 h; Yield given. Multistep reaction;

potassium carbonate in acetone

1.1: N,N,N',N',N'',N''-hexamethylphosphoric triamide; n-butyllithium / tetrahydrofuran; hexane / -40 - 0 °C 1.2: 15 h / 20 °C / |Inert atmosphere 2.1: ammonium cerium (IV) nitrate / acetonitrile; water / 3.5 h / -7 - 20 °C / |Cooling with ice View Scheme

1.1: N,N,N',N',N'',N''-hexamethylphosphoric triamide; n-butyllithium / tetrahydrofuran; hexane / -40 - 0 °C 1.2: 15 h / 20 °C / |Inert atmosphere 2.1: ammonium cerium (IV) nitrate / acetonitrile; water / 3.5 h / -7 - 20 °C / |Cooling with ice View Scheme

1: CrO3, AcOH 2: H2SO4 3: (i) aq. HCl, MeOH, (ii) aq. FeCl3 View Scheme