copper T=230°C;

n-butyllithium; nitrobenzene 1.) THF, hexane, -75 deg C, 50 min.; 2.) -75 deg C, 4h, -> room temp.; Yield given. Multistep reaction;

potassium permanganate; acetone

1: 93 percent / m-chloroperoxybenzoic acid / CHCl3 / 1.5 h / Heating 2: 93 percent / K2CO3 / acetone / 5 h / Ambient temperature 3: 1.) MeLi / 1.) Et2O, 0 deg C, 20 min, 2.) Et2O, 0 deg C, 60 min 4: 1.) n-BuLi / 1.) hexane, Et2O, a) 0 deg C, 10 min, b) RT, 24 h, 2.) hexane, Et2O, 30 min 5: 80 percent / triethylsilane, BF3*Et2O / CH2Cl2 / 0.5 h / -78 °C 6: 56 percent / silver(II) oxide, 7 N aq. nitric acid / dioxane / 0.17 h / Ambient temperature View Scheme

1: 80 percent / 125 °C 2: 1.) butyllithium, B(OBu)3, 2.) 30percent H2O2, 3.) (NH4)2SO4 3: K2CO3 / acetone / 6 h View Scheme

copper T=250°C;

1.1: toluene / 3.5 h / Heating 2.1: n-BuLi / diethyl ether; hexane / -78 °C 2.2: diethyl ether; hexane / -78 - 20 °C 3.1: H2O2 / methanol; H2O / 0.25 h 3.2: 0.91 g / aq. HCl / 100 °C View Scheme

n-butyllithium; nitrobenzene 1.) THF, hexane, -75 deg C, 50 min.; 2.) -75 deg C, 4h, -> room temp.; Yield given. Multistep reaction;