copper(l) iodide; 1,10-phenanthroline in o-xylene T=150°C; 6 h; Inert atmosphere;

1: 1) NaNO2, HCl, 2) 10percent NaOH / 2) EtOH 2: 1) t-BuOK / 1) DMSO, 2) DMSO, irradiation 3: 98 percent / hydrogen, HClO4 / 10percent Pd/C / ethanol / 6 h / 25 °C / 3000.2 Torr 4: 83 percent / t-BuOK / tetrahydrofuran / 0.5 h / 25 °C 5: 88 percent / 10N KOH / tetrahydrofuran / 24 h / 25 °C View Scheme

hydrogenchloride; tin in ethanol

copper(I) oxide; ammonium hydroxide in dimethyl sulfoxide T=90°C; 16 h; Sealed tube;