iodine; 1-(p-methylbenzenesulfonyloxy)-1,2-benziodoxol-3(1H)-one in acetonitrile 16 h; Ambient temperature;

sulfur dioxide; iodine; nitric acid; acetic acid T=220°C;

1: With potassium permanganate; water in tert-butyl alcohol 2: With hydrogenchloride in water; tert-butyl alcohol

sodium hydroxide in water 1 h; Reflux;

magnesium; NiCl2((PPh3)P)2 1) Et2O, 2h, reflux, 2) Et2O, 16h, reflux; Yield given. Multistep reaction;

1: 1) Mg / 2) NiCl2(PPh3)2 / 1) Et2O, 2h, reflux, 2) Et2O, 16h, reflux 2: NBS, benzoylperoxide / CCl4 / 3 h / Heating 3: acetic acid / 22 h / Heating 4: 87 percent / 15percent NaOH / methanol / 6 h / 50 °C 5: 48 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature 6: 1) PhLi / 1) THF, benzene, Et2O, -70 deg C, 2a) THF, -50 deg C, 2 h, 2b) -50 to -10 deg C, 1 h 7: 64 percent / benzene / 144 h / Irradiation 8: 75 percent / DDQ / benzene / 48 h / Heating View Scheme

1: 1) Mg / 2) NiCl2(PPh3)2 / 1) Et2O, 2h, reflux, 2) Et2O, 16h, reflux 2: NBS, benzoylperoxide / CCl4 / 3 h / Heating View Scheme

bromine in ethylene dibromide T=135°C; Inert atmosphere;

N-bromosuccinmide; dibenzoyl peroxide in chloroform UV-irradiation; Title compound not separated from byproducts.;