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.
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.
see article for more examples
proposed, simplified mechanism
vicarious nucleophilic substitution, phenols, tert-butyl hydroperoxide, cumene hydroperoxide