1: With n-butyllithium in tetrahydrofuran; hexane T=-78°C; Metallation; 0.333333 h; 2: With iodine in tetrahydrofuran; hexane T=20°C; Iodination; 1.5 h;

1: With n-butyllithium 2: With potassium hydride; 1,3-diamino-propane 3: With iodine in morpholine

propylamine; anhydrous 1-octyne; hydroxylamine; copper(l) chloride in ethanol Ambient temperature;

propylamine; hydroxylamine; copper(l) chloride in ethanol Ambient temperature;

1: 62 percent / dipotassium azodicarboxylate / methanol; acetic acid / 1 h / Heating 2: 73 percent / bis(acetonitrile)palladium(II) dichloride / dimethylformamide / 36 h / Ambient temperature View Scheme