Hydroxylation of Nitroarenes with Alkyl Hydroperoxide Anions via Vicarious Nucleophilic Substitution of Hydrogen1

Journal of Organic Chemistry

Volumn 55, Issue 17, 1990, Pages 4979-4981

  Maskosza, Mieczyslaw ^a   Sienkiewicz, Krzysztof ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000458735     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00304a001     Document Type: Article

References (27)

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18. Makosza, M.; Sienkiewicz, K. Polish Patent Appl., Nr. PL273927, July 1988; European Patent Appl. Nr. 89112889.4. Recently, similar hydroxylations of some nitroarenes were observed by Mattersteig, G.; Pritzkow, W.; Voerckel, V. J. Prakt. Chem., in press. We are indebted to those authors for consent to cite their results prior to publication.
19. Wohl, A.; Aue, W. Ber. Dtsch. Chem. Ges. 1901, 34, 2442.
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22. SNAr of halogen with highly nucleophilic hydroperoxide anions proceeds faster than with alkoxy or hydroxy anions. Nitroaryl hydroperoxides, although spectroscopically observed, decompose rapidly to form nitrophenols, Heller, R. A.; Weiler, R. Can. J. Chem. 1987, 65, 251.
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