Oxidation of 4-alkyl-1-hydroxyimino-2,4,6-tri-t-butyl-2,5-cyclohexadienes. Formation of 4-alkyl-2,6-di-t-butylnitrobenzenes via iminoxyl radical.

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概要

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• Reactions of 4-alkyl-1-hydroxyimino-2,4,6-tri-<I>t</I>-butyl-2,5-cyclohexadienes (<B>1</B>) with silver(I) oxide afforded 4-alkyl-2,6-di-<I>t</I>-butylnitrobenzenes (<B>2</B>) mainly, which were found to be formed <I>via</I> an iminoxyl radical on the base of the ESR spectra and by-products, 4-alkyl-1-<I>t</I>-butoxyimino-2,4,6-tri-<I>t</I>-butyl-2,5-cyclohexadienes (<B>3</B>). This reaction is a novel oxidative decomposition of iminoxyl radical and provides a practical preparative method for the nitrobenzenes (<B>2</B>). Oxidation of <B>1</B> with other reagents (nickel peroxide and <I>m</I>-chloroperbenzoic acid) and oxidation of 6-alkyl-1-hydroxyimino-2,4,6-tri-<I>t</I>-butyl-2,4-cyclohexadienes (<B>5</B>) have also been described.

• 公益社団法人 日本化学会の論文

著者

• Inamoto Naoki

  Department Of Chemistry Graduate School Of Science The University Of Tokyo

• Okazaki Renji

  Department Of Chemical And Biological Sciences Faculty Of Science Japan Women's University

• Inagaki Yoshio

  Department of Chemistry, Faculty of Science, The University of Tokyo

• Inamoto Naoki

  Department of Chemistry and Research Centre for Spectrochemistry, Faculty of Science, The University of Tokyo

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