in methanol electrolysis; Pb or Hg cathode; other solvent; Product distribution;

1: AcOH / ethanol / 18 h / Heating 2: NaBH4 / methanol / 1 h / Ambient temperature 3: 78 percent / acetic anhydride / 1 h / 70 °C 4: 86 percent / NaIO4 / H2O; methanol / 16 h / Ambient temperature 5: 1.) TFAA, 2.) BF3*Et2O / 1.) benzene, RT, 1 h, 2.) benzene, RT, 2 h 6: 75 percent / NaBH4, NiCl2*6H2O / methanol; tetrahydrofuran / 0.5 h / Ambient temperature 7: 72 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating View Scheme

tetracarbonylbis(μ-chloro)dirhodium(I); di-tert-butyl peroxide; 1,2-bis-(diphenylphosphino)ethane in benzene T=160°C; 12 h; Inert atmosphere; chemoselective reaction;

1: H2O2; H2SO4 / methanol / 48 h / 20 °C 2: H2SO4 / 2 h / 0 °C View Scheme

1: 98 percent / Li / tetrahydrofuran / 1.) -10 deg C to 0 deg C, 2.) 0 deg C, overnight 2: 62 percent / toluene-4-sulphonic acid / ethanol / 1 h / Heating 3: 91 percent / H2, H2SO4 / 10percent Pd/C / ethanol 4: 91 percent / BBr3 / CH2Cl2 / 1.) -80 deg C, 3 d, 2.) 72 h 5: 1.) LiNH2, Fe(NO3)3 / 1.) liq. NH3, THF, HMPA, 2.) liq. NH3, THF, HMPA, 40 deg C, 24 h 6: p-TsOH / ethanol / 3 h / Heating 7: 0.1704 g / PBr3 / CHCl3 / 16 h / -30 deg C to r. t. 8: 1.) EtMgBr, CuCl / 1.) THF, 1 h, 2.) THF, 72 h, 35 deg C 9: 50 percent / H2, quinoline / 5 percent Pd-BaSO4 / ethyl acetate / 2 h / Ambient temperature View Scheme

1: (i) HBr, benzene, (ii) P(OEt)3, (iii) /BRN= 606013/, NaOMe, DMF 2: H2, FeCl3 / PtO2 / aq. ethanol View Scheme