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DMD Oxidation of in-Situ-Generated σH Adducts Derived from Nitroarenes and the Carbanion of 2-Phenylpropionitrile to Phenols:  The First Direct Substitution of a Nitro by a Hydroxy Group

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journal contribution
posted on 30.05.1998 by Waldemar Adam, Mieczysław Ma̧kosza, Krzysztof Staliński, Cong-Gui Zhao
The dimethyldioxirane (DMD) oxidation of σH adducts derived from nitroarenes and the carbanion of 2-phenylpropionitrile yields unexpectedly the phenols 5 as the major products, while the usually observed nitroarenes 4 are formed in very little amounts, if any. The phenol yield was much improved when a small quantity (0.5−1.0 equiv.) of water was added at the start of the reaction. This novel oxidation of Meisenheimer complexes provides the first direct synthesis of phenols from nitroarenes, an unprecendented transformation.

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