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Radical transformations of some N-alkylanilines by their oxidation with different agents: an EPR study

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Abstract

N-Alkylanilines X–NH–Ph (Ph = substituted phenyl ring) with two different types of alkyl substituent X [X = C2H5–CO–CH2CH(Ph), X = CH3, C2H5, CH(CH3)2, CH2C6H5] were oxidized using different agents. While oxidation with 3-chloroperbenzoic acid leads to production of the corresponding aminoxyl radicals X–NO•–Ph, it was confirmed that application of PbO2 resulted in the formation of aminyl radicals X–N•–Ph, as indirectly proved by the spin-trapping method. Contrary to those transformations, with employment of either Pb(OAc)4 or t-BuO •2 radical, reactions taking place on the alkyl substituent were also observed.

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Acknowledgments

This paper was supported by the Ministry of Education of the Czech Republic under research project MSM 0021630501 and the Grant Agency of Slovak Republic (Grant No. 1/0429/11).

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Authors and Affiliations

  1. Faculty of Chemistry, Brno University of Technology, CZ-612 00, Brno, Czech Republic

    Lenka Šafaříková, Ladislav Omelka & Petr Majzlík

  2. Faculty of Pharmacy, Comenius University, SK-835 32, Bratislava, Slovak Republic

    Jan Světlík

Authors
  1. Lenka Šafaříková
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  2. Ladislav Omelka
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  3. Petr Majzlík
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  4. Jan Světlík
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Correspondence to Ladislav Omelka.

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Šafaříková, L., Omelka, L., Majzlík, P. et al. Radical transformations of some N-alkylanilines by their oxidation with different agents: an EPR study. Monatsh Chem 144, 163–169 (2013). https://doi.org/10.1007/s00706-012-0874-6

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  • DOI: https://doi.org/10.1007/s00706-012-0874-6

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