sodium bis(2-methoxyethoxy)aluminium dihydride in toluene 20 h; Heating;

1: 100 percent / n-BuLi / tetrahydrofuran; hexane / 1.) r.t., 30 min, 2.) r.t., 12 h 2: 93.5 percent / n-BuLi / diethyl ether; hexane / 1.) -78 deg C, 1 h, 2.) r.t., 12 h 3: 98 percent / diphenyl phosphorazidate, Et3N / benzene / 1 h / 50 °C 4: 86.4 percent / 1,2-dichloro-benzene / 0.25 h / 190 °C 5: 41.5 percent / NaAlH2(OCH2CH2OCH3)2 / toluene / 20 h / Heating View Scheme

1: 93.5 percent / n-BuLi / diethyl ether; hexane / 1.) -78 deg C, 1 h, 2.) r.t., 12 h 2: 98 percent / diphenyl phosphorazidate, Et3N / benzene / 1 h / 50 °C 3: 86.4 percent / 1,2-dichloro-benzene / 0.25 h / 190 °C 4: 41.5 percent / NaAlH2(OCH2CH2OCH3)2 / toluene / 20 h / Heating View Scheme

1: 98 percent / diphenyl phosphorazidate, Et3N / benzene / 1 h / 50 °C 2: 86.4 percent / 1,2-dichloro-benzene / 0.25 h / 190 °C 3: 41.5 percent / NaAlH2(OCH2CH2OCH3)2 / toluene / 20 h / Heating View Scheme

1: 86.4 percent / 1,2-dichloro-benzene / 0.25 h / 190 °C 2: 41.5 percent / NaAlH2(OCH2CH2OCH3)2 / toluene / 20 h / Heating View Scheme

toluene-4-sulfonic acid in benzene T=100°C; 14 h;

1: pyridine / Heating 2: K2CO3 / acetone / Ambient temperature 3: 68 percent / I2 / H2O; acetic acid / 80 °C 4: 45 percent / trifluoroacetic acid / 2 h / Irradiation 5: Heating View Scheme

1: K2CO3 / acetone / Ambient temperature 2: 68 percent / I2 / H2O; acetic acid / 80 °C 3: 45 percent / trifluoroacetic acid / 2 h / Irradiation 4: Heating View Scheme

1: 68 percent / I2 / H2O; acetic acid / 80 °C 2: 45 percent / trifluoroacetic acid / 2 h / Irradiation 3: Heating View Scheme

1: 72.3 percent / 1.) phosphorus oxychloride / 3 h / 90 °C 2: 54.7 percent / p-toluenesulfonic acid / benzene / 14 h / 100 °C / var. Lewis acid View Scheme