N,N,N',N',N'',N''-hexamethylphosphoric triamide; n-butyllithium 1.) THF, hexane, -78 deg C, 10 min, 2.) THF, hexane, a) from -78 deg C to RT, 2 h, b) RT, 16 h; Multistep reaction;

1.1: LiNH2 / liquid ammonia / -78 °C 1.2: liquid ammonia / -78 - 20 °C View Scheme

n-butyllithium 1.) hexane, 2.) THF/HMPA, 0 deg C, 16 h; Yield given. Multistep reaction;

1: pyridinium toluene-p-sulfonate / methanol / 24 h 2: 70 percent / CBr4; Ph3P / benzene / 3 h 3: 65 percent / Na2S / aq. ethanol / 4 h / 20 °C 4: 70 percent / Oxone / CH2Cl2 / 50 °C 5: 70 percent / KOH-Al2O3; CBr2F2 / CH2Cl2 View Scheme

1: pyridinium p-toluenesulfonate / tetrahydrofuran; ethanol / 48 h / 55 °C 2: lithium aluminum hydride / tetrahydrofuran / Heating View Scheme