1: 86 percent / 1.) n-BuLi, 2.) Li / 1.) THF-hexane, 0 deg C, 2.) NH3 liq.m, -70 deg C, 5 min 2: 75 percent / 1.) n-BuLi / 1.) THF-hexane, -45 deg C, 40 min, 2.) -45 deg C, 40 min; -> 10 deg C 1 h 3: Li / diethyl ether; liquid ammonia / -65 °C / other reagent, solvent, temperature View Scheme

lithium in ammonia T=-70°C; 0.0833333 h;

1: 86 percent / 1.) n-BuLi, 2.) Li / 1.) THF-hexane, 0 deg C, 2.) NH3 liq.m, -70 deg C, 5 min 2: 70 percent / 1.) n-BuLi / 1.) THF-hexane, -45 deg C, 40 min, 2.) -45 deg C, 40 min; -> 10 deg C 1 h 3: Na, DB18C6 / liquid ammonia / 0.17 h / -65 °C View Scheme