in carbon disulfide T=0°C;

aluminium trichloride in carbon disulfide 0.5 h; Ambient temperature;

1: 99 percent / pyridine / 1.) 0 degC, 15 min 2.) room temperature, 12 h 2: 68 percent / AlCl3 / CS2 / 0.5 h / Ambient temperature View Scheme

trifluoroacetic anhydride 48 h; Ambient temperature;

1: 1.) LiAlH4, 2.) pyridine 2: 46 percent / trifluoroacetic anhydride / 48 h / Ambient temperature View Scheme

1: 95 percent / PCl5 / POCl3 / 2 h / 45 - 50 °C 2: 92 percent / NaNH2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) -78 degC 2.) 50 degC, 2 h 3: 94 percent / P(C6H5)3*Br2, collidine / CH2Cl2 / 5 h / Ambient temperature View Scheme

1: 95 percent / PCl5 / POCl3 / 2 h / 45 - 50 °C 2: 92 percent / NaNH2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) -78 degC 2.) 50 degC, 2 h 3: 94 percent / P(C6H5)3*Br2, collidine / CH2Cl2 / 5 h / Ambient temperature 4: 1.) n-butyllithium, HMPA / 1.)THF, hexane, -78 degC to 0 degC 2.) 45-50 degC, 2 h 5: 63 percent / 5percent HCl / tetrahydrofuran; H2O / 2 h / 50 °C View Scheme

N,N,N',N',N'',N''-hexamethylphosphoric triamide; phosphorus pentachloride; sodium amide; trichlorophosphate 1.) 40-50 deg C, 2 h, 2.) THF, 40-50 deg C; Yield given. Multistep reaction;

1: 95 percent / PCl5 / POCl3 / 2 h / 45 - 50 °C 2: 92 percent / NaNH2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) -78 degC 2.) 50 degC, 2 h View Scheme

1: 95 percent / PCl5 / POCl3 / 2 h / 45 - 50 °C 2: 92 percent / NaNH2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) -78 degC 2.) 50 degC, 2 h 4: 72 percent / P(C6H5)3, CBr4 / diethyl ether / 4 h View Scheme