oxalyl dichloride; N,N-dimethyl-formamide in dichloromethane T=0 - 20°C; 0.5 h; Inert atmosphere;

2: 76 percent / SOCl2 3: 79 percent / Mg / 1.) THF, 12 h, 2.) THF, reflux, 12 h 4: 1.) MeI, 2.) 20percent NaOH / 1.) RT, 3 h, 2.) MeOH, water, reflux, 24 h 5: 55 percent / poly(phosphoric)acid / 3 h / Ambient temperature 6: 90 percent / 85percent hydrazine hydrate / ethanol / 14 h / Heating 7: 44 percent / HgO, Na2SO4, 10percent KOH / tetrahydrofuran; ethanol / 12 h / Ambient temperature 8: benzene / 2 h / Irradiation View Scheme

ammonium hydroxide

aluminium trichloride

1.1: 89 percent / toluene / 0 - 20 °C 2.1: sec-BuLi; TMEDA / tetrahydrofuran / 0.75 h / -78 °C 2.2: 40 percent / tert-BuLi / tetrahydrofuran; pentane / -78 - 20 °C View Scheme

hydrogenchloride; aluminium chloride in dichloromethane

1: diethyl ether 2: dioxane; aqueous Na2CO3; Na2S2O3 / weiteres Reagens: Ag2O; View Scheme

sulfuric acid in methanol; acetone

1: 80 percent / diisopropylamine; n-BuLi / tetrahydrofuran; hexane / 5 h / -78 - 0 °C 2: 82 percent / BBr3 / CH2Cl2 / 72 h / 20 °C View Scheme

aluminium trichloride