1: 58 percent / KMnO4 / pyridine; H2O / 20 h / 50 °C 2: 73 percent / N,N'-dicyclohexylcarbodiimide / dioxane; ethyl acetate / 6 h / Ambient temperature View Scheme

1: 38 percent / KMnO4 / pyridine 2: 95 percent / cyanuric fluoride, pyridine / CH2Cl2 / 2 h / -20 - -10 °C 3: 84 percent / LiBH4 / tetrahydrofuran; methanol / 1 h / Ambient temperature View Scheme

potassium permanganate in pyridine; water T=50°C; 20 h;

silver(l) oxide in diethyl ether 1 h;

1: hydroxylamine 2: pyridine 3: NH3 (liquid) 4: I2; Et3N View Scheme

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

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

1.1: n-BuLi / diethyl ether; hexane / 2 h / -40 - 0 °C 1.2: 54 percent / diethyl ether; hexane / 3 h / -60 °C 2.1: hydroxylamine hydrochloride; pyridine / 3 h / 70 °C 3.1: 2.90 g / pyridine / 3 h / Heating 4.1: 77 percent / NH3 / diethyl ether / 12 h / 20 °C 5.1: 82 percent / I2; Et3N / CH2Cl2 View Scheme

N-bromosuccinmide; dibenzoyl peroxide in tetrachloromethane T=70°C; 3 h;