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

1: 93 percent / Ag2O / CHCl3 / 40 - 50 °C 2: 1) Zn; 2) 40 percent NaOH / 1) CHCl3, glacial acetic acid; 2) dioxane, 12 h View Scheme

1: 93 percent / Ag2O / CHCl3 / 40 - 50 °C 2: 1) Zn; 2) 40 percent NaOH / 1) CHCl3, glacial acetic acid; 2) dioxane, 12 h View Scheme

1: 93 percent / Ag2O / CHCl3 / 40 - 50 °C 2: 1) Zn; 2) 40 percent NaOH / 1) CHCl3, glacial acetic acid; 2) dioxane, 12 h 3: 85 percent / bis(trimethylsilyl)cyclohexadiene, iodine / CHCl3 / 0.03 h 4: 1) FeCl3*6H2O; 2) triethylamine, 4-(dimethylamino)pyridine / 2) Zn / 1) acetonitrile, 1 min.; 2) 10 h, room temp. View Scheme

1: 93 percent / Ag2O / CHCl3 / 40 - 50 °C 2: 1) Zn; 2) 40 percent NaOH / 1) CHCl3, glacial acetic acid; 2) dioxane, 12 h 3: 85 percent / bis(trimethylsilyl)cyclohexadiene, iodine / CHCl3 / 0.03 h 4: 1) FeCl3*6H2O; 2) triethylamine, 4-(dimethylamino)pyridine / 2) Zn / 1) acetonitrile, 1 min.; 2) 10 h, room temp. 5: 91 percent / NaOAc, H2 / Pd/C / benzene; methanol / 5 h / 40 °C View Scheme

aluminium trichloride; sodium chloride T=180°C;

hydrogenchloride; sodium hydroxide; copper(l) chloride; sodium nitrite 1.) water, 2.) 60 deg C, 10 min; 100 deg C, 30 min; room temp., 24 h; Yield given. Multistep reaction;

1: 65 percent / fuming sulphuric acid (60percent SO3)/sulphur / 1.) 1 h, 2.) 50 deg C, 10 min, 3.) room temp., 18 h 2: 1.) sodium nitrite, NaOH, aq. HCl, 2.) CuCl, aq. HCl / 1.) water, 2.) 60 deg C, 10 min; 100 deg C, 30 min; room temp., 24 h View Scheme