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toluene-4-sulfonic acid Ambient temperature;

T=200°C;

1: With ozone in methanol; dichloromethane T=-78°C; 2: With sodium tetrahydroborate in methanol; dichloromethane T=-78 - 20°C; 12 h; 3: With water in ethyl acetate

1: NaIO4, OsO4 / H2O; diethyl ether 3: (i) aq. HCl, (ii) NaH View Scheme

1: 76 percent / sodium metaperiodate; ruthenium(III) trichloride monohydrate / CH2Cl2; acetonitrile; H2O / 18 h / 20 °C 2: diethylaminosulfur trifluoride / CH2Cl2 / 18 h / 20 °C View Scheme

1.1: sodium periodate / RuCl3 monohydrate / dichloromethane; acetonitrile; water / 5 - 20 °C 2.1: diethylamino-sulfur trifluoride / dichloromethane / 24 h / -10 - 20 °C 3.1: sodium hydroxide; water / pentane; methanol / 75 h / 20 - 60 °C 3.2: pH 1 4.1: caesium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 5.1: lithium aluminium tetrahydride / tetrahydrofuran / -30 - 20 °C / Inert atmosphere 5.2: 0 °C View Scheme

ethanol; palladium Hydrogenation.Erwaermen des Reaktionsprodukts mit wss. NaOH;

1: aq. KOH / methanol 2: diethyl ether 3: O3, Py / CH2Cl2 / -80 °C View Scheme

1.1: potassium hydroxide; water / ethanol / 6 h / Reflux 1.2: pH 3 - 4 2.1: sodium azide / tetrabutylammomium bromide; zinc trifluoromethanesulfonate / tetrahydrofuran / 40 °C 3.1: tetrahydrofuran / 45 °C View Scheme