sodium tetrahydroborate in 1,4-dioxane; isopropyl alcohol T=20°C; Rate constant;

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

1: 96 percent / hydroxylamine hydrochloride, pyridine / ethanol / 12 h / 60 °C 2: Et3N, (N,N-dimethylamino)pyridine / CH2Cl2 / 0.75 h / Ambient temperature 3: liq. NH3 / CH2Cl2 / 18 h / Ambient temperature 4: 77 percent / tert-butyl hypochlorite, Et3N / ethanol; 2-methyl-propan-2-ol / 2 h / Ambient temperature 5: 1.) thallium(III) trifluoroacetate, 2.) PdCl2, LiCl, MgO / 1.) TFA, r.t., 24 h, 2.) r.t., 43 h View Scheme

1: 96 percent / hydroxylamine hydrochloride, pyridine / ethanol / 12 h / 60 °C 2: Et3N, (N,N-dimethylamino)pyridine / CH2Cl2 / 0.75 h / Ambient temperature 3: liq. NH3 / CH2Cl2 / 18 h / Ambient temperature 4: 77 percent / tert-butyl hypochlorite, Et3N / ethanol; 2-methyl-propan-2-ol / 2 h / Ambient temperature 5: 1.) thallium(III) trifluoroacetate, 2.) PdCl2, LiCl, MgO / 1.) TFA, r.t., 24 h, 2.) r.t., 43 h 6: 98 percent / BBr3 / CH2Cl2 / 0.5 h / 0 °C View Scheme

1: 92 percent / NH2OH*HCl; C5H5N 2: 93 percent / C5H5N 3: 88 percent / NH3 4: 73 percent / I2; Et3N / methanol View Scheme

1: toluene / 24 h / 120 °C 2: (R)-3,3′-bis[3,5-bis(trifluoromethyl)phenyl]-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate; 2-(4-nitrophenyl)-2,3-dihydrobenzothiazole / dichloromethane / 24 h / 55 °C / Inert atmosphere 3: sulfuric acid; periodic acid / water; acetonitrile / 24 h / 20 °C View Scheme