benzoylchlorobis(triphenylphosphine)palladium(II) in chloroform T=65°C; 5 h;

aluminium trichloride in N,N-dimethyl-formamide T=90°C; 1 h; Yield given;

1: thionyl chloride 2: 2.954 g / AlCl3 / 2 h / 20 - 60 °C View Scheme

diethyl ether; phenyl-Cd-phenyl

1: 85 percent / dimethylsulfoxide / 2 h / 80 °C 2: 95 percent / NH2NH2*H2O, KOH / bis-(2-hydroxy-ethyl) ether / 4 h / Heating 3: 95 percent / diethyl ether / 12 h / 0 °C 4: 90 percent / LiAlH4 / diethyl ether / 4 h / Heating 5: 88 percent / Me3SiI / CH2Cl2 / 24 h / Ambient temperature 6: 1.) n-BuLi / 1.) THF, -78 deg C, 60 min, 2.) THF, a) -78 deg C, 30 min, b) RT, 45 min 7: 89 percent / concd H2SO4 / 24 h / Heating 8: 95 percent / LiAlH4 / diethyl ether / 4 h / Heating 9: 85 percent / Me3SiI / CH2Cl2 / 24 h / Ambient temperature 10: 82 percent / dimethylsulfoxide / 2 h / 80 °C 11: 91 percent / KOH / ethane-1,2-diol / 6 h / Heating 12: 95 percent / diethyl ether / 12 h / 0 °C 13: 1.) Tl(OCOCF3)3, 2.) aq. KI / 1.) TFA, RT, 5 d, 2.) TFA, 15 min 14: 95 percent / 1 N NaOH / ethanol / 1.5 h / Heating View Scheme

1: 85 percent / dimethylsulfoxide / 2 h / 80 °C 2: 95 percent / NH2NH2*H2O, KOH / bis-(2-hydroxy-ethyl) ether / 4 h / Heating 3: 95 percent / diethyl ether / 12 h / 0 °C 4: 90 percent / LiAlH4 / diethyl ether / 4 h / Heating 5: 88 percent / Me3SiI / CH2Cl2 / 24 h / Ambient temperature 6: 1.) n-BuLi / 1.) THF, -78 deg C, 2.) THF, a) -78 deg C, 10 min, b) from -78 deg C to RT 7: 86 percent / concd H2SO4 / 24 h / Heating 8: 1.) Tl(OCOCF3)3, 2.) aq. KI / 1.) TFA, RT, 5 d, 2.) TFA, 15 min 9: 90 percent / 1 N NaOH / ethanol / 1.5 h / Heating View Scheme

1: 99 percent / AcOH / Heating 2: 28 percent / hydrazine hydrate; KOH / bis-(2-hydroxy-ethyl) ether / 1 h / Heating View Scheme