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Study of the effect of annelation on the rearrangement of 1,2-dialkylpyridinium salts by the MO LCAO self-consistent field (SCF) method

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Abstract

The anhydro bases formed from 1,2-dialkylquinolinium (I), 1,2-dialkylisoquinolinium (II), and 2,3-dialkylisoquinolinium (III) salts were calculated within the framework of the π-electron approximation of the MO LCAO self-consistent field (SCF) method. It is shown that, in contrast to II and III, I does not undergo recyclization; annelation of the pyridine ring facilitates recyclization. The recyclization indexes are linked with the aromatic character of the pyridine ring and increase as the aromatic character decreases.

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Authors and Affiliations

  1. Institute of Physical Organic Chemistry and Coal Chemistry, Academy of Sciences of the Ukrainian SSR, 340048, Donetsk

    Yu. B. Vysotskii, B. P. Zemskii, T. V. Stupnikova & R. S. Sagitullin

  2. Donetsk State University, 340055, Donetsk

    Yu. B. Vysotskii, B. P. Zemskii, T. V. Stupnikova & R. S. Sagitullin

  3. M. V. Lomonosov Moscow State University, 117234, Moscow

    Yu. B. Vysotskii, B. P. Zemskii, T. V. Stupnikova & R. S. Sagitullin

Authors
  1. Yu. B. Vysotskii
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  2. B. P. Zemskii
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  3. T. V. Stupnikova
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  4. R. S. Sagitullin
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Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 381–386, March, 1980.

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Vysotskii, Y.B., Zemskii, B.P., Stupnikova, T.V. et al. Study of the effect of annelation on the rearrangement of 1,2-dialkylpyridinium salts by the MO LCAO self-consistent field (SCF) method. Chem Heterocycl Compd 16, 288–292 (1980). https://doi.org/10.1007/BF02401729

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  • DOI: https://doi.org/10.1007/BF02401729

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