1.1: anhydrous iron chloride / ethanol / 15 h / 20 °C / Inert atmosphere 2.1: lithium aluminium tetrahydride / diethyl ether / 0.5 h / 0 °C / Inert atmosphere 3.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 20 °C / Inert atmosphere 4.1: hydroxylamine hydrochloride; sodium hydrogencarbonate / ethanol / 1 h / 20 °C / Inert atmosphere 5.1: hydrogenchloride; Pearlman's catalyst; hydrogen / methanol; water / 12 h / 30 °C / 760.05 Torr 6.1: triethylamine / N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere 7.1: manganese(IV) oxide / dichloromethane / 20 °C / Inert atmosphere 8.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 0.5 h / 20 °C / Inert atmosphere 9.1: boron trifluoride diethyl etherate / dichloromethane / 0.67 h / -78 °C / Inert atmosphere 9.2: -78 °C / Inert atmosphere 10.1: 1,3,5-trimethyl-benzene / 6 h / 160 - 170 °C / Sealed tube; Inert atmosphere 11.1: acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,4-dioxane / 0.5 h / 20 °C / Inert atmosphere 11.2: 1 h / 20 °C / Inert atmosphere 12.1: K2OsO4*2H2O; (DHQD)2-PYR; methanesulfonamide; potassium carbonate; potassium hexacyanoferrate(III) / water; tert-butyl alcohol / 48 h / 0 °C / Inert atmosphere 13.1: iodine; calcium carbonate / methanol; water / 15 h / 40 °C / Inert atmosphere 14.1: hydrogen bromide / water / 5 h / 110 °C / Sealed tube; Inert atmosphere View Scheme

1.1: anhydrous iron chloride / ethanol / 15 h / 20 °C / Inert atmosphere 2.1: lithium aluminium tetrahydride / diethyl ether / 0.5 h / 0 °C / Inert atmosphere 3.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 20 °C / Inert atmosphere 4.1: hydroxylamine hydrochloride; sodium hydrogencarbonate / ethanol / 1 h / 20 °C / Inert atmosphere 5.1: hydrogenchloride; Pearlman's catalyst; hydrogen / methanol; water / 12 h / 30 °C / 760.05 Torr 6.1: triethylamine / N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere 7.1: manganese(IV) oxide / dichloromethane / 20 °C / Inert atmosphere 8.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 0.5 h / 20 °C / Inert atmosphere 9.1: boron trifluoride diethyl etherate / dichloromethane / 0.67 h / -78 °C / Inert atmosphere 9.2: -78 °C / Inert atmosphere 10.1: 1,3,5-trimethyl-benzene / 6 h / 160 - 170 °C / Sealed tube; Inert atmosphere 11.1: acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,4-dioxane / 0.5 h / 20 °C / Inert atmosphere 11.2: 1 h / 20 °C / Inert atmosphere 12.1: K2OsO4*2H2O; (DHQD)2-PYR; methanesulfonamide; potassium carbonate; potassium hexacyanoferrate(III) / water; tert-butyl alcohol / 48 h / 0 °C / Inert atmosphere 13.1: iodine; calcium carbonate / methanol; water / 15 h / 40 °C / Inert atmosphere 14.1: hydrogen bromide / water / 5 h / 110 °C / Sealed tube; Inert atmosphere View Scheme

1: 2.) p-TsOH*H2O / 1.) toluene, reflux, 0.5 h, 2.) toluene, reflux, 3 h 2: 46.9 percent / H2 / PtO2*H2O / ethanol; dioxane / 6 h / Irradiation 3: 47percent aq.HBr / 3 h / Heating View Scheme

1: 63 percent / p-TsOH / toluene / Heating 2: 47 percent / H2 / PtO2 View Scheme

toluene-4-sulfonic acid in toluene Heating;

toluene-4-sulfonic acid in toluene 4 h; Heating;

hydrogen; palladium on activated charcoal in ethanol 4 h;

1: ethyl bromide With magnesium in tetrahydrofuran 0.833333 h; Inert atmosphereReflux; 2: 2-amino-5-methoxybenzonitrile in tetrahydrofuran T=5 - 20°C; 3: With hydrogenchloride; water in tetrahydrofuran T=0 - 20°C;

1: 100 percent / tetrahydrofuran / 3.5 h 2: 88 percent / Jones reagent / acetone / 0.17 h / Ambient temperature 3: 98 percent / H2 / 10percent Pd(C) / ethanol / 4 h View Scheme

1: 88 percent / Jones reagent / acetone / 0.17 h / Ambient temperature 2: 98 percent / H2 / 10percent Pd(C) / ethanol / 4 h View Scheme