mercury(II) diacetate 48 h; Heating;

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: 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: 5 mg / dimethylformamide / 3 h / 70 - 90 °C View Scheme

1: 30 percent / 1.) n-BuLi; 3.) H2O / 1.) pentane, 0 deg C, 6 h; 2.) diethyl ether, 0 deg C, 12 h 2: 91 percent / Hg(OAc)2 / dioxane; H2O / 3 h / Ambient temperature View Scheme