1: With sodium hypochlorite T=5 - 10°C; 0.5 h; Industry scale; 2: With sodium hydroxide in water T=10 - 25°C; 20.5 - 24.5 h; Industry scale; Product distribution / selectivity;

in dichloromethane T=60°C; Heating / reflux;

sodium hypochlorite; sodium hydroxide in methanol T=25°C; Hofmann rearrangement; 24 h;

1: sulfuric acid / acetic acid / 1 h / 100 °C 2: sodium hypochlorite; sodium hydroxide / methanol / 24 h / 25 °C View Scheme

1: 1,3,5,7-tetra-azatricyclo[5.1.1.13,5]decane / 18 h / 115 °C 2: 1,4-diaza-bicyclo[2.2.2]octane / 16 h / Reflux 3: sulfuric acid / acetic acid / 1 h / 100 °C 4: sodium hypochlorite; sodium hydroxide / methanol / 24 h / 25 °C View Scheme

1: 1,4-diaza-bicyclo[2.2.2]octane / 16 h / Reflux 2: sulfuric acid / acetic acid / 1 h / 100 °C 3: sodium hypochlorite; sodium hydroxide / methanol / 24 h / 25 °C View Scheme

1: hydrogen / methanol / 20 h / 80 °C / 22502.3 Torr 2: water; potassium hydroxide / methanol / 24 h / Reflux 3: bromine / water / 2 h / 0 - 5 °C View Scheme

1: hydrogen / methanol / 20 h / 80 °C / 22502.3 Torr 2: water; potassium hydroxide / methanol / 24 h / Reflux 3: ethanol; water / 1 h / 20 °C 4: acetic acid / 2 - 4 h / 100 °C 5: sodium tetrahydroborate / dichloromethane; water; isopropyl alcohol / 16 h / 20 - 25 °C View Scheme