1: thionyl chloride / 3 h / Reflux 2: ammonium hydroxide / 0 - 5 °C 3: trichlorophosphate / 24 h / 20 °C / Cooling with ice; Reflux View Scheme

1: H2SO4 / 1 h / Heating 2: NH2NH2 / methanol / 2 h / Heating View Scheme

1.1: hydrogenchloride / methanol / 18 h / Reflux 2.1: dichloromethane / 3 h / 25 °C / Cooling with ice 3.1: potassium hydroxide; copper (II) acetate monohydrate / ethanol / 18 h / 90 °C / Inert atmosphere 4.1: water / tetrahydrofuran / 72 h / 25 °C 4.2: pH 0 5.1: triethylamine; diphenyl phosphoryl azide / ethyl acetate; n-heptane; tert-butyl alcohol; methanol / 24 h / 25 °C / Reflux View Scheme

1: thionyl chloride / 3 h / |Reflux 2: ammonium hydroxide / 0 - 5 °C 3: trichlorophosphate / 24 h / |Reflux 4: N-bromosuccinmide; 2,2'-azo-bisisobutyronitrile / tetrachloromethane / 2 h / |Reflux View Scheme

1.1: hydrogenchloride / methanol / 18 h / Reflux 2.1: dichloromethane / 3 h / 25 °C / Cooling with ice 3.1: potassium hydroxide; copper (II) acetate monohydrate / ethanol / 18 h / 90 °C / Inert atmosphere 4.1: water; lithium hydroxide hydrate / tetrahydrofuran / 4 h / 25 °C 4.2: pH 0 5.1: triethylamine; diphenyl phosphoryl azide / tert-butyl alcohol / 18 h / 25 °C / Reflux View Scheme

thionyl chloride in dichloromethane T=20°C; 3 h;

1: 62 percent / hydrogen chloride (gas) / 4 h / Heating 2: N-chlorosuccinimide, azobisisobutyronitrile / acetic acid; CCl4 / 60 °C / Irradiation View Scheme

1: With borane-THF in tetrahydrofuran T=5 - 25°C; 18 h; Inert atmosphere; 2: With hydrogenchloride in tetrahydrofuran; 1,4-dioxane 0.5 h;