silver(l) oxide in chloroform T=40 - 50°C;

ammonium cerium(IV) nitrate; water in acetonitrile

1: 35 percent / AlCl3, NaCl / 180 °C 2: 93 percent / Ag2O / CHCl3 / 40 - 50 °C View Scheme

sodium hydroxide; water; zinc 1) CHCl3, glacial acetic acid; 2) dioxane, 12 h; Yield given. Multistep reaction;

sodium hydroxide; zinc 1) CHCl3, glacial acetic acid; 2) dioxane, 12 h; Yield given. Multistep reaction;

sodium hydroxide; zinc 1) CHCl3, glacial acetic acid; 2) dioxane, 12 h; Yield given. Multistep reaction;

1: 1) Zn; 2) 40 percent NaOH / 1) CHCl3, glacial acetic acid; 2) dioxane, 12 h 2: 85 percent / bis(trimethylsilyl)cyclohexadiene, iodine / CHCl3 / 0.03 h 3: 1) FeCl3*6H2O; 2) triethylamine, 4-(dimethylamino)pyridine / 2) Zn / 1) acetonitrile, 1 min.; 2) 10 h, room temp. View Scheme

1: 1) Zn; 2) 40 percent NaOH / 1) CHCl3, glacial acetic acid; 2) dioxane, 12 h 2: 85 percent / bis(trimethylsilyl)cyclohexadiene, iodine / CHCl3 / 0.03 h 3: 1) FeCl3*6H2O; 2) triethylamine, 4-(dimethylamino)pyridine / 2) Zn / 1) acetonitrile, 1 min.; 2) 10 h, room temp. 4: 91 percent / NaOAc, H2 / Pd/C / benzene; methanol / 5 h / 40 °C View Scheme