1: 73 percent / LiNH2/NH3 2: 98 percent / I2, Ph3P, imidazole / CH2Cl2 3: 1.) t-BuLi / 1.) Et2O, -78 deg C, 2.) Et2O 4: 92 percent / tetrahydrofuran / 0 °C 5: 75 percent / MeLi / tetrahydrofuran / 0 °C 6: 1.) n-BuLi, 2.) Me2AlCl View Scheme

1: 41 percent / LiNH2/NH3 2: 36 percent / Li, 1,3-diaminopropane, t-BuOK 3: 73 percent / LiNH2/NH3 4: 98 percent / I2, Ph3P, imidazole / CH2Cl2 5: 1.) t-BuLi / 1.) Et2O, -78 deg C, 2.) Et2O 6: 92 percent / tetrahydrofuran / 0 °C 7: 75 percent / MeLi / tetrahydrofuran / 0 °C 8: 1.) n-BuLi, 2.) Me2AlCl View Scheme

1: 1.) t-BuLi / 1.) Et2O, -78 deg C, 2.) Et2O 2: 92 percent / tetrahydrofuran / 0 °C 3: 75 percent / MeLi / tetrahydrofuran / 0 °C 4: 1.) n-BuLi, 2.) Me2AlCl View Scheme

1: 36 percent / Li, 1,3-diaminopropane, t-BuOK 2: 73 percent / LiNH2/NH3 3: 98 percent / I2, Ph3P, imidazole / CH2Cl2 4: 1.) t-BuLi / 1.) Et2O, -78 deg C, 2.) Et2O 5: 92 percent / tetrahydrofuran / 0 °C 6: 75 percent / MeLi / tetrahydrofuran / 0 °C 7: 1.) n-BuLi, 2.) Me2AlCl View Scheme

1: 98 percent / I2, Ph3P, imidazole / CH2Cl2 2: 1.) t-BuLi / 1.) Et2O, -78 deg C, 2.) Et2O 3: 92 percent / tetrahydrofuran / 0 °C 4: 75 percent / MeLi / tetrahydrofuran / 0 °C 5: 1.) n-BuLi, 2.) Me2AlCl View Scheme

1: 92 percent / tetrahydrofuran / 0 °C 2: 75 percent / MeLi / tetrahydrofuran / 0 °C 3: 1.) n-BuLi, 2.) Me2AlCl View Scheme

n-butyllithium; dimethylaluminum chloride Yield given. Multistep reaction;