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Basicities and transformations of pyrylium and pyridinium salts containing p-aminophenyl substituents

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Abstract

On the basis of the measured basicity constants of pyrylium and pyridinium salts containing p-aminophenyl substituents it is shown that the positive charge in the pyrylium cation is considerably higher than in the pyridinium cation. The σ constants of the pyrylium and pyridinium substituents, which show that the magnitude of the electronic effect of the pyrylium ring is considerably higher than that of the pyrydinium ring, were calculated. The reaction of the indicated pyrylium salts with some electrophilic and nucleophilic reagents was examined.

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Literature cited

  1. W. Dilthey and C. Berres, J. Prakt. Chen., 111, 340 (1925).

    Google Scholar 

  2. F. Kŕóhnke and K. Dickore, Ber., 92, 46 (1959).

    Google Scholar 

  3. V. A. Bren', E. I. Malysheva, and V. I. Minkin, Reakts. Sposobn. Org. Soedin., No. 4, 523 (1967).

    Google Scholar 

  4. É. A. Zvezdina, M. P. Zhdanova, V. A. Bren', and G. N. Dorofeenko, Khim. Geterotsikl. Soedin., No. 11, 1461 (1974).

    Google Scholar 

  5. A. T. Balaban, Tetrahedron, 24, 5059 (1968).

    Google Scholar 

  6. G. N. Dorofeenko, É. A. Zvezdina, and V. V. Derbenev, Zh. Org. Khim., 9, 1079 (1973).

    Google Scholar 

  7. V. I. Minkin and V. A. Bren', Reakts. Sposobn. Org. Soedin., No. 4, 112 (1967).

    Google Scholar 

  8. W. Dilthey, G. Frode, H. Koenen, J. Prakt. Chem., 114, 153 (1926).

    Google Scholar 

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1025–1028, August, 1976.

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Zvezdina, É.A., Derbenev, V.V., Bren, V.A. et al. Basicities and transformations of pyrylium and pyridinium salts containing p-aminophenyl substituents. Chem Heterocycl Compd 12, 847–850 (1976). https://doi.org/10.1007/BF00510097

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  • DOI: https://doi.org/10.1007/BF00510097

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