lithium in diethyl ether Barbier reaction; Heatingsonication;

1: diethyl ether / 0.5 h / 0 °C 2: 61 percent / lithium / diethyl ether / Heating; sonication View Scheme

1: 80 percent / sodium azide / dimethylsulfoxide / 72 h / 25 °C 2: 100 percent / diethyl ether / 3 h / Ambient temperature 3: 1.) PPh3 / 1.) Et2), RT, 4 h, 2.) Et2O, RT, overnight 4: 1.) aq. KOH, 2.) 10percent aq. HCl / 1.) EtOH, RT, 1 h, 2.) EtOH, reflux, 2 h View Scheme

1: 100 percent / diethyl ether / 3 h / Ambient temperature 2: 1.) PPh3 / 1.) Et2), RT, 4 h, 2.) Et2O, RT, overnight 3: 1.) aq. KOH, 2.) 10percent aq. HCl / 1.) EtOH, RT, 1 h, 2.) EtOH, reflux, 2 h View Scheme

hydrogenchloride; potassium hydroxide 1.) EtOH, RT, 1 h, 2.) EtOH, reflux, 2 h; Yield given. Multistep reaction;

1: 1.) PPh3 / 1.) Et2), RT, 4 h, 2.) Et2O, RT, overnight 2: 1.) aq. KOH, 2.) 10percent aq. HCl / 1.) EtOH, RT, 1 h, 2.) EtOH, reflux, 2 h View Scheme

ammonia; lithium in tetrahydrofuran others nitriles and Grinard reagent, various reaction conditions; Mechanism;