sodium azide; sodium nitrite Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

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1.1: 95 percent / pyridine / 20 °C 2.1: 72 percent / m-iodoxybenzoic acid; diphenyl diselenide / toluene / 12 h / Heating 3.1: hydrazine hydrate / ethane-1,2-diol / 1 h / Heating 3.2: 95 percent / potassium hydroxide / ethane-1,2-diol; H2O / 5 h / 195 - 197 °C View Scheme

1.1: 95 percent / pyridine / 20 °C 2.1: 72 percent / m-iodoxybenzoic acid; diphenyl diselenide / toluene / 12 h / Heating 3.1: hydrazine hydrate / ethane-1,2-diol / 1 h / Heating 3.2: 95 percent / potassium hydroxide / ethane-1,2-diol; H2O / 5 h / 195 - 197 °C 4.1: pyridine; ammonium chloride / 125 - 135 °C 4.2: acetic acid; chromium trioxide / H2O; 1,2-dichloro-ethane / 1 h / 20 °C 4.3: 57 percent / aluminium oxide / benzene / 2 h 5.1: 91.7 percent / hydrogen peroxide; sodium hydroxide / methanol / 2 h / 20 °C 6.1: 95 percent / pyridine / 20 °C 7.1: 70 percent / triethyl orthoformate; p-toluenesulfonic acid / CH2Cl2 / 20 h / 20 °C 8.1: 72 percent / tetrahydrofuran; diethyl ether / 72 h / 60 °C 9.1: m-iodoxybenzoic acid; diphenyl diselenide / toluene / 22 h / Heating 9.2: 50 percent / p-toluenesulfonic acid / CH2Cl2 / 4 h / 20 °C 10.1: perchloric acid; 1,3-dibromo-5,5-dimethylhydantoin / dimethylformamide / 3 h / cooling 10.2: 75.8 percent / sodium hydroxide / CH2Cl2; methanol; H2O / 2 h / cooling 11.1: 80 percent / hydrofluoric acid / tetrahydrofuran; CH2Cl2 / 5 h / -70 - 0 °C 12.1: 100 percent / anhydrous calcium chloride; calcium oxide; iodine / methanol / 1 h / 25 - 27 °C 13.1: 180 mg / acetic acid / acetone; H2O / 3 h / Heating 14.1: 90 percent / sodium methoxide; methanol / 4 h / 25 °C View Scheme

pyridine T=20°C;

1.1: 95 percent / pyridine / 20 °C 2.1: 72 percent / m-iodoxybenzoic acid; diphenyl diselenide / toluene / 12 h / Heating 3.1: hydrazine hydrate / ethane-1,2-diol / 1 h / Heating 3.2: 95 percent / potassium hydroxide / ethane-1,2-diol; H2O / 5 h / 195 - 197 °C 4.1: pyridine; ammonium chloride / 125 - 135 °C 4.2: acetic acid; chromium trioxide / H2O; 1,2-dichloro-ethane / 1 h / 20 °C 4.3: 57 percent / aluminium oxide / benzene / 2 h 5.1: 91.7 percent / hydrogen peroxide; sodium hydroxide / methanol / 2 h / 20 °C 6.1: 95 percent / pyridine / 20 °C 7.1: 70 percent / triethyl orthoformate; p-toluenesulfonic acid / CH2Cl2 / 20 h / 20 °C 8.1: 72 percent / tetrahydrofuran; diethyl ether / 72 h / 60 °C 9.1: m-iodoxybenzoic acid; diphenyl diselenide / toluene / 22 h / Heating 9.2: 50 percent / p-toluenesulfonic acid / CH2Cl2 / 4 h / 20 °C 10.1: perchloric acid; 1,3-dibromo-5,5-dimethylhydantoin / dimethylformamide / 3 h / cooling 10.2: 75.8 percent / sodium hydroxide / CH2Cl2; methanol; H2O / 2 h / cooling 11.1: 80 percent / hydrofluoric acid / tetrahydrofuran; CH2Cl2 / 5 h / -70 - 0 °C 12.1: 100 percent / anhydrous calcium chloride; calcium oxide; iodine / methanol / 1 h / 25 - 27 °C 13.1: 180 mg / acetic acid / acetone; H2O / 3 h / Heating View Scheme

2: ethanol; aqueous hydrochloric acid View Scheme

ethanol; hydrazine hydrate; ethylene glycol in wss. Alkalilauge;

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