1: aqueous acetone; sodium azide 2: benzene 3: water; ammonia View Scheme

1: 40.2 g / AlCl3 / CH2Cl2 / 3 h / 20 °C 2: 95 percent / n-butylnitrite; conc. aq. HCl / methanol / 0.5 h / 40 °C View Scheme

[rhenium(pentacarbonyl)(bromide)] in 1,2-dichloro-ethane 2 h; Heating;

1: 40.2 g / AlCl3 / CH2Cl2 / 3 h / 20 °C 2: 95 percent / n-butylnitrite; conc. aq. HCl / methanol / 0.5 h / 40 °C 3: H2; H2SO4 / 10percent Pd/C / acetic acid / 7 h / 2585.81 Torr View Scheme

1: AlCl3, aluminium chloride / dichloromethane / 2 h / 0 - 20 °C / |Inert atmosphere 2: sodium hydride / paraffin oil / 90 °C / |Inert atmosphere 3: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C / |Inert atmosphere 4: pyridinium p-toluenesulfonate / toluene / |Inert atmosphere; |Reflux; |Dean-Stark 5: diisobutylaluminium hydride / dichloromethane; toluene / 3 h / -78 °C / |Inert atmosphere 6: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 1.5 h / -78 - 20 °C / |Inert atmosphere 7: AD-mix-βreg;; methanesulfonamide; osmium(VIII) oxide / dichloromethane; #tert!-butyl alcohol; water / 72 h / 20 °C / |Inert atmosphere 8: pyridinium p-toluenesulfonate / toluene / 2 h / 90 °C / |Inert atmosphere 9: lithium hydroxide hydrate / methanol; tetrahydrofuran / 0.5 h / 20 °C / |Inert atmosphere 10: boron tribromide / dichloromethane / -78 - 20 °C / |Inert atmosphere View Scheme

1: NaN3 / acetone; H2O 2: benzene / Heating View Scheme

1: aqueous acetone; sodium azide 2: benzene 3: aqueous hydrochloric acid View Scheme

2: rhodium(II) acetate / CH2Cl2 / Heating View Scheme

1: AlCl3, aluminium chloride / dichloromethane / 2 h / 0 - 20 °C / |Inert atmosphere 2: sodium hydride / paraffin oil / 90 °C / |Inert atmosphere View Scheme

ammonia in tetrahydrofuran T=0°C;