sodium amide in paraffin T=160°C; 1 h;

ammonia; sodium amide in diethyl ether 1 h;

sodium amide 1.) mineral oil, 160 deg C, 1 h, 2.) Et2O, 60 h; Yield given. Multistep reaction. Yields of byproduct given;

sodium amide 1.) mineral oil, 160 deg C, 1 h, 2.) Et2O, 60 h; Yield given. Multistep reaction. Yields of byproduct given;

1: 1.) sodium amide / 1.) mineral oil, 160 deg C, 1 h, 2.) Et2O, 60 h 2: 80 percent / Cu2Cl2 / acetonitrile / 12 h / Ambient temperature 3: 77 percent / diisobutylaluminium hydride / pentane / 10 h / Ambient temperature 4: bromine / CHCl3 / -80 °C 5: 18 percent Chromat. / 18-crown-6, KOH / hexane / no (R)-3-phenylbut-1-yne production; no desired product with sodium amide/liquid NH3 (by contrast, successful dehydrobromination for gomologous 1,2-dibromides) View Scheme