ammonia in dichloromethane T=-78°C; 12 h;

1: 92 percent / NH2OH*HCl; C5H5N 2: 93 percent / C5H5N 3: 88 percent / NH3 View Scheme

1: 93 percent / C5H5N 2: 88 percent / NH3 View Scheme

1: 77 percent / n-BuLi 2: 92 percent / NH2OH*HCl; C5H5N 3: 93 percent / C5H5N 4: 88 percent / NH3 View Scheme

1: 99 percent / KOH / tetrahydrofuran / 16 h 2: 88 percent / n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 °C 3: 97 percent / NH2OH*HCl; NaOH / ethanol / Heating 4: 98 percent / NEt3; DMAP / CH2Cl2 / 36 h / 20 °C / in the dark 5: 99 percent / NH3 / CH2Cl2 / 12 h / -78 °C View Scheme

1: 77 percent / tert-butyl hypochlorite, Et3N / ethanol; 2-methyl-propan-2-ol / 2 h / Ambient temperature 2: 1.) thallium(III) trifluoroacetate, 2.) PdCl2, LiCl, MgO / 1.) TFA, r.t., 24 h, 2.) r.t., 43 h View Scheme

1: 77 percent / tert-butyl hypochlorite, Et3N / ethanol; 2-methyl-propan-2-ol / 2 h / Ambient temperature 2: 1.) thallium(III) trifluoroacetate, 2.) PdCl2, LiCl, MgO / 1.) TFA, r.t., 24 h, 2.) r.t., 43 h 3: 98 percent / BBr3 / CH2Cl2 / 0.5 h / 0 °C View Scheme

silver(l) oxide in diethyl ether 20 h; in the dark;