pyridine 3 h; Heating;

1: hydroxylamine 2: pyridine View Scheme

1: 83 percent / n-BuLi 2: hydroxylamine; pyridine / ethanol 3: pyridine View Scheme

1: 91 percent / liq. NH3 / diethyl ether / 12 h / Ambient temperature 2: 91 percent / Ag2O / diethyl ether / 1 h 3: 58 percent / KMnO4 / pyridine; H2O / 20 h / 50 °C 4: 73 percent / N,N'-dicyclohexylcarbodiimide / dioxane; ethyl acetate / 6 h / Ambient temperature View Scheme

1: NH3 (liquid) 2: I2; Et3N 3: KMnO4; pyridine View Scheme

ammonia in diethyl ether T=-78°C;

1: NH3 (liquid) 2: I2; Et3N View Scheme

1: 76 percent / NH3 2: 59 percent / N-bromosuccinimide; AIBN View Scheme