pyridine; ammonium cerium(IV) nitrate in water; acetone T=68°C; pH=4.4; 4 h; Product distribution; Further Variations:Reagentsreaction time;

1.1: NaH; n-Bu4NI / dimethylformamide / 20 °C 2.1: 10.5 g / HCl / H2O; methanol / 3 h 3.1: 97 percent / NaIO4 / H2O; methanol / 1 h / 20 °C 4.1: 77 percent / BF3*OEt2 / CH2Cl2 / 2 h / -78 °C 5.1: 97 percent / NaH; n-Bu4NI / 16 h / 20 °C 6.1: IDCP / CH2Cl2 / 1 h / 20 °C 7.1: 7.8 g / Zn / aq. ethanol / 1 h / Heating 8.1: 9-BBN / tetrahydrofuran / 0 - 20 °C 8.2: 86 percent / aq. H2O2; aq. NaOH / 0 °C 9.1: 84 percent / DMSO; (COCl)2; Et3N / CH2Cl2 / -78 - 20 °C 10.1: DDQ; Et3N / CH2Cl2; H2O / 3 h / 20 °C 11.1: 69 percent / HCO2NH4; NaCNBH3; 4 Angstroem MS / methanol / 24 h / 20 °C 12.1: HCOOH / Pd/C / methanol / 2 h 13.1: 39 mg / 6N HCl / tetrahydrofuran / 2 h / 20 °C View Scheme

1: tetrahydrofuran; toluene / 3.25 h / -60 - 0 °C / Reflux; Inert atmosphere 2: N-bromosuccinmide; silver nitrate / acetone / 2 h / 20 °C / Inert atmosphere; Darkness 3: acetic acid / water / 60 h / 40 °C 4: ozone / dimethylsulfide; water / 1 h / 20 °C View Scheme

1: 69 percent / NaH / dimethylformamide 2: 100 percent / 70 percent aq. AcOH / 20 °C 3: 96 percent / NaIO4 / H2O; methanol / 0 °C View Scheme

1: 69 percent / NaH / dimethylformamide 2: 100 percent / 70 percent aq. AcOH / 20 °C View Scheme

sodium hydride in N,N-dimethyl-formamide

18-crown-6 ether; potassium hydroxide in tetrahydrofuran T=20°C; 16 h;

sodium hydride in N,N-dimethyl-formamide; paraffin 6 h; Ambient temperature;

1: PPh3, EtO2CNNCO2Et / tetrahydrofuran 2: 75 percent / 30percent SnCl4 / CH2Cl2 / 24 h / Ambient temperature View Scheme