1: palladium 10 on activated carbon; sodium carbonate / ethylene glycol dimethyl ether; water / 40 - 45 °C / Inert atmosphere 2: hydrogenchloride; water / methanol / 12 h / 50 °C View Scheme

1: n-butyllithium / tetrahydrofuran; diethyl ether; hexane / 1 h / -100 - -78 °C / Inert atmosphere; Cooling with liquid nitrogen/methanol 2: ammonium chloride / tetrahydrofuran; diethyl ether; hexane / 1 h / 20 °C / Inert atmosphere; Saturated solution 3: palladium 10 on activated carbon; sodium carbonate / ethylene glycol dimethyl ether; water / 40 - 45 °C / Inert atmosphere 4: hydrogenchloride; water / methanol / 12 h / 50 °C View Scheme

1: iodine; silver(I) acetate / chloroform / 5 h / 20 °C / Inert atmosphere 2: n-butyllithium / tetrahydrofuran; diethyl ether; hexane / 1 h / -100 - -78 °C / Inert atmosphere; Cooling with liquid nitrogen/methanol 3: ammonium chloride / tetrahydrofuran; diethyl ether; hexane / 1 h / 20 °C / Inert atmosphere; Saturated solution 4: palladium 10 on activated carbon; sodium carbonate / ethylene glycol dimethyl ether; water / 40 - 45 °C / Inert atmosphere 5: hydrogenchloride; water / methanol / 12 h / 50 °C View Scheme

1.1: acetyl chloride; zinc dibromide / dichloromethane / 3 h / 20 °C / Inert atmosphere 1.2: 3 h / Inert atmosphere; Cooling with ice 2.1: iodine; silver(I) acetate / chloroform / 5 h / 20 °C / Inert atmosphere 3.1: n-butyllithium / tetrahydrofuran; diethyl ether; hexane / 1 h / -100 - -78 °C / Inert atmosphere; Cooling with liquid nitrogen/methanol 4.1: ammonium chloride / tetrahydrofuran; diethyl ether; hexane / 1 h / 20 °C / Inert atmosphere; Saturated solution 5.1: palladium 10 on activated carbon; sodium carbonate / ethylene glycol dimethyl ether; water / 40 - 45 °C / Inert atmosphere 6.1: hydrogenchloride; water / methanol / 12 h / 50 °C View Scheme

aluminium trichloride; benzene

1: 37 percent / pyridine / diethyl ether / 5.5 h / 2 - 5 °C 2: 18 percent / BF3-etherate / dioxane / 6 h / 51 - 53 °C 3: 50 percent / 4percent aq. NaOH / methanol / 1.5 h / 50 °C View Scheme

2,3-dicyano-5,6-dichloro-p-benzoquinone in tetrahydrofuran T=60°C; 0.75 h; Inert atmosphere;