1: 82 percent / Ag2O / CHCl3 / 40 - 50 °C 2: 1) Zn; 2) NaOH / 1) CHCl3, glacial acetic acid; 2) dioxane, H2O, 12 h 3: 59 percent / bis(trimethylsilyl)cyclohexadiene, iodine / CHCl3 / 0.03 h View Scheme

1: 1) Zn; 2) NaOH / 1) CHCl3, glacial acetic acid; 2) dioxane, H2O, 12 h 2: 59 percent / bis(trimethylsilyl)cyclohexadiene, iodine / CHCl3 / 0.03 h View Scheme

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

1: 86 percent / FeCl3*6H2O / acetonitrile 2: 70 percent / 4-(dimethylamino)pyridine, triethylamine / 15 h / Ambient temperature 3: 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. 4: 65 percent / 10 percent ammonium cer(IV) nitrate (aq.) / acetonitrile 5: 70 percent / conc. H2SO4 / 0.08 h View Scheme

1: 70 percent / 4-(dimethylamino)pyridine, triethylamine / 15 h / Ambient temperature 2: 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. 3: 65 percent / 10 percent ammonium cer(IV) nitrate (aq.) / acetonitrile 4: 70 percent / conc. H2SO4 / 0.08 h View Scheme

1: 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. 2: 65 percent / 10 percent ammonium cer(IV) nitrate (aq.) / acetonitrile 3: 70 percent / conc. H2SO4 / 0.08 h View Scheme

sulfuric acid 0.0833333 h;

1: 1) Zn; 2) conc. NaOH / 1) CH3OH, CHCl3, glacial acetic acid; 2) dioxane, H2O, 12 h 2: bis(trimethylsilyl)cyclohexadiene, iodine / CHCl3 / 0.03 h View Scheme

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

1: 65 percent / 10 percent ammonium cer(IV) nitrate (aq.) / acetonitrile 2: 70 percent / conc. H2SO4 / 0.08 h View Scheme