pyridine; lead(IV) acetate; copper diacetate in benzene 3 h; Heating;

potassium hydroxide

1: 60 percent / Pb(OAc)4, Cu(OAc)2*H2O, Py / benzene / 3 h / Heating 2: 25.3 g / Br2 / CH2Cl2 / 0.5 h / 20 °C 3: 80 percent / t-BuOK, dibenzo-18-crown-6 / hexane / 24 h / Heating View Scheme

1: 60 percent / Pb(OAc)4, Cu(OAc)2*H2O, Py / benzene / 3 h / Heating 2: 25.3 g / Br2 / CH2Cl2 / 0.5 h / 20 °C 3: 80 percent / t-BuOK, dibenzo-18-crown-6 / hexane / 24 h / Heating 4: 92 percent / TsOH / diethyl ether / 20 h / 20 °C View Scheme

1: 60 percent / Pb(OAc)4, Cu(OAc)2*H2O, Py / benzene / 3 h / Heating 2: 25.3 g / Br2 / CH2Cl2 / 0.5 h / 20 °C 3: 80 percent / t-BuOK, dibenzo-18-crown-6 / hexane / 24 h / Heating 4: 92 percent / TsOH / diethyl ether / 20 h / 20 °C 5: Li, FeCl3, liq. NH3 / 1 h / -33 °C 6: tetrahydrofuran; dimethylsulfoxide View Scheme

1: 60 percent / Pb(OAc)4, Cu(OAc)2*H2O, Py / benzene / 3 h / Heating 2: 25.3 g / Br2 / CH2Cl2 / 0.5 h / 20 °C 3: 80 percent / t-BuOK, dibenzo-18-crown-6 / hexane / 24 h / Heating 4: 92 percent / TsOH / diethyl ether / 20 h / 20 °C 5: Li, FeCl3, liq. NH3 / 1 h / -33 °C 6: 14.55 g / tetrahydrofuran; dimethylsulfoxide 7: 84 percent / TsOH / methanol; H2O / 20 h / 20 °C View Scheme

water; potassium carbonate Electrolysis.und Behandlung des Reaktionsprodukts mit warmer wss.-aethanol.Kalilauge;

(i) Na, MeOH, (electrolysis), (ii) KOH, EtOH; Multistep reaction;

1: alcoholic KOH-solution View Scheme

1: 60 percent / Pb(OAc)4, Cu(OAc)2*H2O, Py / benzene / 3 h / Heating 2: 25.3 g / Br2 / CH2Cl2 / 0.5 h / 20 °C 3: 80 percent / t-BuOK, dibenzo-18-crown-6 / hexane / 24 h / Heating 4: 92 percent / TsOH / diethyl ether / 20 h / 20 °C 5: Li, FeCl3, liq. NH3 / 1 h / -33 °C 6: tetrahydrofuran; dimethylsulfoxide 7: TsOH / methanol; H2O / 20 °C 8: 1.) i-BuMgBr, 2.) Cp2TiCl2, 3.) Py / 1.) Et2O, 0 deg C, 15 min, 2.) 20 deg C, 3 h, 3.) 24 h View Scheme