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Reaction of o-Quinones in Cyclohexane Solutions with Alkyl Radicals Generated by Solution γ-Irradiation

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Abstract

The structures of products formed in reactions of tert-butylated o-quinones with alkyl radicals were determined by 1H and 13C NMR and two-dimensional 1H-1H NOESY spectroscopy, and also by gas chromatography-mass spectrometry. The major products formed upon γ-irradiation of deaerated solutions of 4-tert-butyl-1,2-benzoquinone and 3,5-di-tert-butyl-1,2-benzoquinone in cyclohexane are monoalkyl ethers and products of addition to the C=C bond. In the case of 4-tert-butyl-1,2-benzoquinone, these are products of mixed O-C and C-C alkylation; the adduct formed by addition of the cyclohexyl radical to the C=C bond in 3,5-di-tert-butyl-1,2-benzoquinone gives an unsymmetrical dimer whose structure was proved by single-crystal X-ray diffraction.

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Authors and Affiliations

  1. Research Institute of Physicochemical Problems, Belarussian State University, Minsk, Belarus

    L. A. Maslovskaya

  2. Institute of Organic Chemistry, University of Gottingen, Gottingen, Germany

    A. I. Savchenko

Authors
  1. L. A. Maslovskaya
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  2. A. I. Savchenko
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__________

Translated from Zhurnal Obshchei Khimii, Vol. 75, No. 9, 2005, pp. 1510–1517.

Original Russian Text Copyright © 2005 by Maslovskaya, Savchenko.

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Maslovskaya, L.A., Savchenko, A.I. Reaction of o-Quinones in Cyclohexane Solutions with Alkyl Radicals Generated by Solution γ-Irradiation. Russ J Gen Chem 75, 1437–1444 (2005). https://doi.org/10.1007/s11176-005-0442-4

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  • DOI: https://doi.org/10.1007/s11176-005-0442-4

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