1: 1.) BF3*Et2O, NaBH4, 2.) Jones reagent / 1.) THF, 18-22 deg C, 11 h, 2.) 0 deg C to 20 deg C, 1 h, 2 h 2: 60 percent / Pb(OAc)4, Cu(OAc)2*H2O, Py / benzene / 3 h / Heating View Scheme

1: ZnCl2 2: (i) KOH, HOCH2CH2OH, (ii) H2, Raney-Ni 3: aq. HBr / Heating View Scheme

1: 1.) BF3*Et2O, NaBH4, 2.) Jones reagent / 1.) THF, 18-22 deg C, 11 h, 2.) 0 deg C to 20 deg C, 1 h, 2 h 2: 60 percent / Pb(OAc)4, Cu(OAc)2*H2O, Py / benzene / 3 h / Heating 3: 25.3 g / Br2 / CH2Cl2 / 0.5 h / 20 °C 4: 80 percent / t-BuOK, dibenzo-18-crown-6 / hexane / 24 h / Heating View Scheme

1: 1.) BF3*Et2O, NaBH4, 2.) Jones reagent / 1.) THF, 18-22 deg C, 11 h, 2.) 0 deg C to 20 deg C, 1 h, 2 h 2: 60 percent / Pb(OAc)4, Cu(OAc)2*H2O, Py / benzene / 3 h / Heating 3: 25.3 g / Br2 / CH2Cl2 / 0.5 h / 20 °C 4: 80 percent / t-BuOK, dibenzo-18-crown-6 / hexane / 24 h / Heating 5: 92 percent / TsOH / diethyl ether / 20 h / 20 °C View Scheme

1: 1.) BF3*Et2O, NaBH4, 2.) Jones reagent / 1.) THF, 18-22 deg C, 11 h, 2.) 0 deg C to 20 deg C, 1 h, 2 h 2: 60 percent / Pb(OAc)4, Cu(OAc)2*H2O, Py / benzene / 3 h / Heating 3: 25.3 g / Br2 / CH2Cl2 / 0.5 h / 20 °C 4: 80 percent / t-BuOK, dibenzo-18-crown-6 / hexane / 24 h / Heating 5: 92 percent / TsOH / diethyl ether / 20 h / 20 °C 6: Li, FeCl3, liq. NH3 / 1 h / -33 °C 7: tetrahydrofuran; dimethylsulfoxide View Scheme

1: 1.) BF3*Et2O, NaBH4, 2.) Jones reagent / 1.) THF, 18-22 deg C, 11 h, 2.) 0 deg C to 20 deg C, 1 h, 2 h 2: 60 percent / Pb(OAc)4, Cu(OAc)2*H2O, Py / benzene / 3 h / Heating 3: 25.3 g / Br2 / CH2Cl2 / 0.5 h / 20 °C 4: 80 percent / t-BuOK, dibenzo-18-crown-6 / hexane / 24 h / Heating 5: 92 percent / TsOH / diethyl ether / 20 h / 20 °C 6: Li, FeCl3, liq. NH3 / 1 h / -33 °C 7: 14.55 g / tetrahydrofuran; dimethylsulfoxide 8: 84 percent / TsOH / methanol; H2O / 20 h / 20 °C View Scheme

9-borabicyclo[3.3.1]nonane dimer; dihydrogen peroxide; sodium acetate 1.) THF, 25 deg C, 2 h, 2.) room temp.; Product distribution;

1: AcOH / 210 - 215 °C 2: KOH / ethane-1,2-diol / Heating 3: H2 / Raney-Ni / ethanol View Scheme

1: dibenzoyl peroxide; hydrogen bromide / und Erwaermen des Reaktionsprodukts mit Methanol (oder Aethanol) unter Zusatz von Toluol-4-sulfonsaeure 2: diethylene glycol; potassium fluoride / 110 °C 3: phosphorus (III)-bromide 4: aqueous ethanol View Scheme

1: 1.) BF3*Et2O, NaBH4, 2.) Jones reagent / 1.) THF, 18-22 deg C, 11 h, 2.) 0 deg C to 20 deg C, 1 h, 2 h 2: 60 percent / Pb(OAc)4, Cu(OAc)2*H2O, Py / benzene / 3 h / Heating 3: 25.3 g / Br2 / CH2Cl2 / 0.5 h / 20 °C 4: 80 percent / t-BuOK, dibenzo-18-crown-6 / hexane / 24 h / Heating 5: 92 percent / TsOH / diethyl ether / 20 h / 20 °C 6: Li, FeCl3, liq. NH3 / 1 h / -33 °C 7: tetrahydrofuran; dimethylsulfoxide 8: TsOH / methanol; H2O / 20 °C 9: 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