pyridine-SO3 complex; triethylamine in dichloromethane; dimethyl sulfoxide T=0°C; 2 h; Inert atmosphere;

.mu.-benzylidene tricobalt nonacarbonyl; hydrogen in toluene T=100°C; P=7600.51 Torr; 10 h;

1: 1.) t-BuOK / 1.) DMSO, RT, 20 min, 2.) DMSO, RT, 2 h 2: AcCl / 2 h / Heating 3: H2 / 5percent Pd/C / methanol / 1 h / Ambient temperature 4: LiAlH4 / diethyl ether / 1 h / Heating 5: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -40 deg C, 25 min, 2.) CH2Cl2, -40 deg C, 5 min View Scheme

1: N-bromosuccinimide, benzoyl peroxide / benzene / 2 h / Heating 2: MeONa, 2-nitropropane / methanol / 7 h / 20 - 40 °C 3: 1.) t-BuOK / 1.) DMSO, RT, 20 min, 2.) DMSO, RT, 2 h 4: AcCl / 2 h / Heating 5: H2 / 5percent Pd/C / methanol / 1 h / Ambient temperature 6: LiAlH4 / diethyl ether / 1 h / Heating 7: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -40 deg C, 25 min, 2.) CH2Cl2, -40 deg C, 5 min View Scheme

1: MeONa, 2-nitropropane / methanol / 7 h / 20 - 40 °C 2: 1.) t-BuOK / 1.) DMSO, RT, 20 min, 2.) DMSO, RT, 2 h 3: AcCl / 2 h / Heating 4: H2 / 5percent Pd/C / methanol / 1 h / Ambient temperature 5: LiAlH4 / diethyl ether / 1 h / Heating 6: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -40 deg C, 25 min, 2.) CH2Cl2, -40 deg C, 5 min View Scheme

hydrogen; RhH(CO)(triphenylphosphine)3 in toluene T=25°C; P=760 Torr; 20 h; Product distribution; Further Variations:CatalystsTemperatures;