n-butyllithium in diethyl ether T=-78°C; 0.0333333 h;

ethene; boron triiodide in dichloromethane T=-20°C;

1: 35 percent / 1.) n-butyllithium, 2.) ethylene iodochloride / tetrahydrofuran / 1.) room temperature, 35 min, 2.) 0 deg C, 0.5 h 2: 83 percent / pyridinium chlorochromate / acetone; CH2Cl2 3: 86 percent / BBr3 / CH2Cl2 / 4 h / Ambient temperature 4: imidazole / dimethylformamide / 10.5 h / 50 °C 7: 88 percent / diethyl ether / 1 h / Ambient temperature 8: 88 percent / I2 / benzene / 1 h / Heating 9: 19 mg / n-butyllithium / diethyl ether / 0.03 h / -78 °C View Scheme

1: imidazole / dimethylformamide / 10.5 h / 50 °C 4: 88 percent / diethyl ether / 1 h / Ambient temperature 5: 88 percent / I2 / benzene / 1 h / Heating 6: 19 mg / n-butyllithium / diethyl ether / 0.03 h / -78 °C View Scheme

1: 86 percent / BBr3 / CH2Cl2 / 4 h / Ambient temperature 2: imidazole / dimethylformamide / 10.5 h / 50 °C 5: 88 percent / diethyl ether / 1 h / Ambient temperature 6: 88 percent / I2 / benzene / 1 h / Heating 7: 19 mg / n-butyllithium / diethyl ether / 0.03 h / -78 °C View Scheme

1: 83 percent / pyridinium chlorochromate / acetone; CH2Cl2 2: 86 percent / BBr3 / CH2Cl2 / 4 h / Ambient temperature 3: imidazole / dimethylformamide / 10.5 h / 50 °C 6: 88 percent / diethyl ether / 1 h / Ambient temperature 7: 88 percent / I2 / benzene / 1 h / Heating 8: 19 mg / n-butyllithium / diethyl ether / 0.03 h / -78 °C View Scheme

1: 1.) n-butyllithium, 2.) ethylene iodochloride / 1.) pentane, 0 deg C, 6 h, 2.) ether, from 0 deg C to 15 deg C, 2 h 2: 85 percent / Hg(OAc)2 / methanol / 0.5 h 3: 83 percent / pyridinium chlorochromate / acetone; CH2Cl2 4: 86 percent / BBr3 / CH2Cl2 / 4 h / Ambient temperature 5: imidazole / dimethylformamide / 10.5 h / 50 °C 8: 88 percent / diethyl ether / 1 h / Ambient temperature 9: 88 percent / I2 / benzene / 1 h / Heating 10: 19 mg / n-butyllithium / diethyl ether / 0.03 h / -78 °C View Scheme

1: 85 percent / Hg(OAc)2 / methanol / 0.5 h 2: 83 percent / pyridinium chlorochromate / acetone; CH2Cl2 3: 86 percent / BBr3 / CH2Cl2 / 4 h / Ambient temperature 4: imidazole / dimethylformamide / 10.5 h / 50 °C 7: 88 percent / diethyl ether / 1 h / Ambient temperature 8: 88 percent / I2 / benzene / 1 h / Heating 9: 19 mg / n-butyllithium / diethyl ether / 0.03 h / -78 °C View Scheme

3: 88 percent / diethyl ether / 1 h / Ambient temperature 4: 88 percent / I2 / benzene / 1 h / Heating 5: 19 mg / n-butyllithium / diethyl ether / 0.03 h / -78 °C View Scheme

1: 88.5 percent / DIBAL/hexane / diethyl ether / 0.17 h / 0 °C 2: 87.5 percent / Br2, (Ph)3P / acetonitrile / Ambient temperature 3: 88 percent / tetrahydrofuran 4: 1.) n-butyllithium / 1.) THF, -78 deg C, 4 h, 2.) THF, overnight 5: 19 mg / n-butyllithium / diethyl ether / 0.03 h / -78 °C View Scheme