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

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Mieczysław Makosza* and Krzysztof Sienkiewicz^†

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

J. Org. Chem., 1998, 63 (13), pp 4199–4208

DOI: 10.1021/jo970726m

Publication Date (Web): June 5, 1998

Section:

Benzene, Its Derivatives, and Condensed Benzenoid Compounds

Abstract

Carbo- and heterocyclic 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. Orientation of the hydroxylation can be controlled to a substantial extent by selection of the proper conditions. Basic mechanistic features of this process were clarified.

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Published In Issue June 26, 1998
Received April 3, 197

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

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Recommend & Share

Related Content

Hydroxylation of nitroarenes with alkylhydroperoxide anions via vicarious nucleophilic substitution of hydrogen

Discovery of Aminofurazan-azabenzimidazoles as Inhibitors of Rho-Kinase with High Kinase Selectivity and Antihypertensive Activity

Design and Synthesis of Novel Human Epidermal Growth Factor Receptor 2 (HER2)/Epidermal Growth Factor Receptor (EGFR) Dual Inhibitors Bearing a Pyrrolo[3,2-d]pyrimidine Scaffold

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