1: 82 percent / Ag2O / CHCl3 / 40 - 50 °C 2: 1) Zn; 2) NaOH / 1) CHCl3, glacial acetic acid; 2) dioxane, H2O, 12 h View Scheme

1: 82 percent / Ag2O / CHCl3 / 40 - 50 °C 2: 1) Zn; 2) NaOH / 1) CHCl3, glacial acetic acid; 2) dioxane, H2O, 12 h View Scheme

sodium hydroxide; zinc 1) CHCl3, glacial acetic acid; 2) dioxane, H2O, 12 h; Yield given. Multistep reaction;

hydrogen; palladium on activated charcoal in methanol; benzene Ambient temperature;

1: 90 percent / H2 / 10 percent Pd/C / benzene; methanol / Ambient temperature 2: 86 percent / FeCl3*6H2O / acetonitrile 3: 70 percent / 4-(dimethylamino)pyridine, triethylamine / 15 h / Ambient temperature 4: 16 percent / H2, sodium acetate / 10 percent Pd/C / benzene; methanol / 40 °C View Scheme

1: 90 percent / H2 / 10 percent Pd/C / benzene; methanol / Ambient temperature 2: 86 percent / FeCl3*6H2O / acetonitrile 3: 70 percent / 4-(dimethylamino)pyridine, triethylamine / 15 h / Ambient temperature 4: 1) sodium acetate, H2; 2) 4-(dimethylamino)pyridine, triethyl amine / 1) 10 percent Pd/C / 1) benzene, CH3OH, 40 deg C; 2) 15 h at room temp. 5: 65 percent / 10 percent ammonium cer(IV) nitrate (aq.) / acetonitrile View Scheme

1: 59 percent / bis(trimethylsilyl)cyclohexadiene, iodine / CHCl3 / 0.03 h View Scheme

bis(trimethylsilyl)cyclohexadiene; iodine in chloroform 0.0333333 h;