Abstract
The nitration method of aromatic compounds using a mixture of metal nitrates and acetic anhydride, commonly called the Menke method, was applied for the synthesis of 5- and 3-nitroacenaphthenes. 5-Nitroacenaphthene was obtained in a yield of ca. 90% even at 30°C, when an amount of metal nitrate equivalent to the acenaphthene dissolved in acetic anhydride was added. However, 3-nitroacenaphthene was formed together with the 5-isomer by the reversed treatment at -10°C in a yield of 18%. Of various metal nitrates tested, cupric and zinc nitrates proved most satisfactory.
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