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Hydroxylation of Nitroarenes with Alkyl Hydroperoxide Anions via Vicarious Nucleophilic Substitution of Hydrogen

Mieczysław Makosza* and Krzysztof Sienkiewicz

*Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44, 01-224 Warsaw, Poland

M. Makosza, K. Sienkiewicz, J. Org. Chem., 1998, 63, 4199-4208.

DOI: 10.1021/jo970726m


Nitroarenes react with anions of tert-butyl and cumyl hydroperoxides in the presence of strong bases to form substituted o- and p-nitrophenols. The reaction usually proceeds in high yields and is of practical value as a method of synthesis and manufacturing of nitrophenols.

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proposed, simplified mechanism

Key Words

vicarious nucleophilic substitution, phenols, tert-butyl hydroperoxide, cumene hydroperoxide

ID: J42-Y1998-630