1: 57 percent / p-toluenesulfonic acid / methanol / 4 h / 60 °C 2: 91 percent / H2, quinoline / Pd/CaCO3 / hexane 3: 82 percent / pyridine / CH2Cl2 / 5 h / Ambient temperature View Scheme

1: H2, 1,2-diaminoethane / P2-Ni / ethanol 2: 89 percent / PPh3, CBr4 / CH2Cl2 / 1.) from 0 deg C to 20 deg C, 1 h, 2) 20 deg C, 14 h 3: 1.) butyllithium, HMPA, 2.) HMPA / 1.) THF, hexane, -20 deg C, 1 h, 2.) RT, 4 h View Scheme

1: 85 percent / p-TsOH / diethyl ether / 5 h / 0 - 3 °C 2: 1.) LiNH2 / 1.) THF, 1.5 h, 2.) 4 h 3: Dowex W-50 (H+ form) / methanol / 20 h 4: H2, 1,2-diaminoethane / P2-Ni / ethanol 5: 89 percent / PPh3, CBr4 / CH2Cl2 / 1.) from 0 deg C to 20 deg C, 1 h, 2) 20 deg C, 14 h 6: 1.) butyllithium, HMPA, 2.) HMPA / 1.) THF, hexane, -20 deg C, 1 h, 2.) RT, 4 h View Scheme

1: 1.) LiNH2 / 1.) THF, 1.5 h, 2.) 4 h 2: Dowex W-50 (H+ form) / methanol / 20 h 3: H2, 1,2-diaminoethane / P2-Ni / ethanol 4: 89 percent / PPh3, CBr4 / CH2Cl2 / 1.) from 0 deg C to 20 deg C, 1 h, 2) 20 deg C, 14 h 5: 1.) butyllithium, HMPA, 2.) HMPA / 1.) THF, hexane, -20 deg C, 1 h, 2.) RT, 4 h View Scheme

1: 85 percent / p-toluenesulfonic acid / diethyl ether / 1 h / Ambient temperature 2: 1.) n-BuLi / 1.) THF-HMPA-hexane, 0 deg C, 30 min, 2.) 25 deg C, 20 h View Scheme

1: 89 percent / PPh3, CBr4 / CH2Cl2 / 1.) from 0 deg C to 20 deg C, 1 h, 2) 20 deg C, 14 h 2: 1.) butyllithium, HMPA, 2.) HMPA / 1.) THF, hexane, -20 deg C, 1 h, 2.) RT, 4 h View Scheme

1: 1.) NaNH2, HMPA / 1.) THF, RT, 90 min, 2.) THF, from -78 deg C to RT, 5 h 2: 89 percent / CBr4, Ph3P / CH2Cl2 / Ambient temperature 3: 1.) n-BuLi / 1.) hexane, THF, -10 deg C, 30 min, 2.) hexane, THF, HMPA, -10 deg C, 3 h View Scheme

1: 89 percent / CBr4, Ph3P / CH2Cl2 / Ambient temperature 2: 1.) n-BuLi / 1.) hexane, THF, -10 deg C, 30 min, 2.) hexane, THF, HMPA, -10 deg C, 3 h View Scheme

1: 1.) NaNH2, HMPA / 1.) THF, RT, 90 min, 2.) THF, from -78 deg C to RT, 5 h 2: 89 percent / CBr4, Ph3P / CH2Cl2 / Ambient temperature 3: 1.) n-BuLi / 1.) hexane, THF, -10 deg C, 30 min, 2.) hexane, THF, HMPA, -10 deg C, 3 h View Scheme

1: 1.) liq. NH3, Fe(NO3)3, Li / 1.) THF, 1 h, 2.) THF, 2 h 2: 77 percent / triethylamine / CH2Cl2 / 2 h 3: 1.) Mg, 2.) Li2CuCl4 / 1.) THF, -10 deg, 30 min, 2.) THF, -10 deg C, 3 h View Scheme