1: 30 percent / triphenylphosphine, CH3I, diethyl azodicarboxylate / tetrahydrofuran / 16 h / Ambient temperature 2: 80 percent / tributyltin hydride, 2,2'-azobisisobutyronitrile / benzene / 2 h / Heating 3: OsO4, NaIO4 4: KMnO4 5: 82 percent / dimethylformamide; acetic acid / 1 h / 80 °C 6: 85 percent / aq. (NH4)2Ce(NO3)6 / acetonitrile / 0.75 h / -5 °C View Scheme

in acetic acid; acetonitrile Kolbe-type electrolysis, Pt electrodes, undivided cell;

1: 93 percent / NaI / acetone / 12 h / Heating 2: 80 percent / tributyltin hydride, 2,2'-azobisisobutyronitrile / benzene / 2 h / Heating 3: OsO4, NaIO4 4: KMnO4 5: 82 percent / dimethylformamide; acetic acid / 1 h / 80 °C 6: 85 percent / aq. (NH4)2Ce(NO3)6 / acetonitrile / 0.75 h / -5 °C View Scheme

1: 1.) Na, liq. NH3, 2.) KMnO4, acetic acid, Adogen 464 / 1.) Et2O, -78 deg C, 30 min, 2.) CH2Cl2, H2O, reflux 2: 84 percent / acetonitrile; acetic acid / Kolbe-type electrolysis, Pt electrodes, undivided cell View Scheme

1: 100 percent / n-Bu4NF / tetrahydrofuran / 0.5 h / 0 °C 2: 1.) Na, liq. NH3, 2.) KMnO4, acetic acid, Adogen 464 / 1.) Et2O, -78 deg C, 30 min, 2.) CH2Cl2, H2O, reflux 3: 84 percent / acetonitrile; acetic acid / Kolbe-type electrolysis, Pt electrodes, undivided cell View Scheme

1: 62 percent / t-BuMgCl / diethyl ether; tetrahydrofuran / 3 h / 0 °C 2: 100 percent / n-Bu4NF / tetrahydrofuran / 0.5 h / 0 °C 3: 1.) Na, liq. NH3, 2.) KMnO4, acetic acid, Adogen 464 / 1.) Et2O, -78 deg C, 30 min, 2.) CH2Cl2, H2O, reflux 4: 84 percent / acetonitrile; acetic acid / Kolbe-type electrolysis, Pt electrodes, undivided cell View Scheme