Nucleophilic photosubstitutions of o-methoxynitrobenzenes

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Abstract
We report a new synthesis of 3-nitroveratrole, based on the directed lithiation of veratrole, and photochemical substitutions of both 3-nitroveratrole and o-nitroanisole with several nucleophiles. Both aromatic substrates undergo photocyanation meta to the nitro group. With hydroxide ion, 3-nitroveratrole reacts meta to the nitro group, but 2-nitroanisole undergoes replacement of either substituent, the proportion of reaction at each site depending upon the OH− concentration. 3-Nitroveratrole undergoes an inefficient reaction with butylamine at each methoxy group; this reaction is apparently second order in amine. The reaction between o-nitroanisole and diethylamine results only in photohydrolysis. Keywords: photosubstitution, nucleophilic, 3-nitroveratrole, o-nitroanisole.

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