1: 81 percent / Br2 / acetate buffer / 47 h / 20 °C / pH 4 2: 40 percent / aq. K2CO3 / Pd(PPh3)4 / 1,2-dimethoxy-ethane / 16 h / 90 °C View Scheme

in N,N-dimethyl-formamide T=85°C; 3.5 h;

in methanol; N,N-dimethyl-formamide T=70°C; 1 h; Further byproducts given;

in N,N-dimethyl-formamide T=70°C; 0.5 h; Further byproducts given;

in water 3 h; Ambient temperaturepH 5.0;

T=130°C; pH=7; 24 h; aq. bufferSealed tube; KineticsThermodynamic data; pH-valueTemperatureTime;

1.1: 50 percent / pyridine / 20 °C 2.1: 100 percent / pyridine / 1 h / 0 - 20 °C 3.1: 100 percent / pyridine / 2 h / 0 - 20 °C 4.1: 100 percent / p-toluenesulfonic acid; EtOH / 1 h / 0 - 20 °C 5.1: 99 percent / Dess-Martin periodinane / CH2Cl2 / 72 h / 0 - 20 °C 6.1: CeCl3 / tetrahydrofuran / 4 h / -78 °C 6.2: 82 percent / tetrahydrofuran / 3 h / -78 °C 7.1: 82 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 8.1: 99 percent / AlCl3 / diethyl ether / 1 h / 0 - 20 °C 9.1: 97 percent / pyridine / 0 - 20 °C 10.1: ozone / CH2Cl2 / 1 h / -78 °C 10.2: 69 percent / Me2S / CH2Cl2 / 1 h / -78 - 20 °C 11.1: 91 percent / KMnO4; phosphate buffer / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C / pH 7 12.1: NEt3; phenyl dichlorophosphate / tetrahydrofuran / 1 h / 0 °C 12.2: 72 percent / NEt3 / tetrahydrofuran / 0.5 h / 0 °C 13.1: 86 percent / trifluoroacetic acid; water / 0.5 h / 20 °C 14.1: 84 percent Spectr. / Bu3SnH / methanol / 3 h / 20 °C / Photolysis View Scheme

1: imidazole / dimethylformamide / 0 °C 2: imidazole / dimethylformamide / 60 °C 3: 76 percent / pyridine 4: HF; pyridine / CH2Cl2 / 0 °C 5: 90 percent / pyridine / 0 °C View Scheme

1: 88 percent / thionyl chloride / hexamethylphosphoric acid triamide / 2 h / 0 °C / r.t., overnight 2: 80 percent / hydrogen chloride / acetone; dimethylformamide / Ambient temperature 3: liquid ammonia / 5 h / Heating 4: 75.5 percent / 0.1 M sulfuric acid / 40 °C / overnight View Scheme

1: pyridine / 20 - 60 °C 2: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 20 °C 3: methanol; ammonia / 48 h / 20 °C View Scheme