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Basicities of stereoisomeric derivatives of piperidine and the stereopolar effect

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The basicities of the geometrical isomers of some piperidine derivatives in 50% (by volume) aqueous methanol at 25° were studied. Compounds with an axial OH group have higher basicities than their epimers with an equatorial OH group. The observed principles can be explained either by the existence of two other effects that are responsible for the different effectiveness of transmission of the induction effect from the axial and equatorial positions or by the variable magnitude of the stereopolar effect, which changes as a result of geminal interaction of the substituents attached to C4 of the piperidine ring.

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Literature cited

  1. D. V. Sokolov, G. S. Litvinenko, V. I. Artyukhin, and A. A. Andrusenko, Izv. Akad. Nauk KazSSR, Ser. Khim., No. 4, 73 (1965).

    Google Scholar 

  2. T. D. Sokolova, S. V. Bogatkov, Yu. F. Malina, B. V. Unkovskii, and E. M. Cherkasova, Reakts. Sposobnost' Organ. Soedin., 4, 68, 445 (1967); 5, 160 (1968).

    Google Scholar 

  3. T. D. Sokolova, S. V. Bogatkov, Yu. F. Malina, and B, V. Unkovskii, Reakts. Sposobnost' Organ. Soedin., 7, 626 (1970).

    Google Scholar 

  4. G. S. Litvinenko, V. I. Artyukhin, A. A. Andrusenko, D. V. Sokolov, V. V. Sosnova, and M. M. Akimova, Reakts. Sposobnost' Organ. Soedin., 7, 960 (1970).

    Google Scholar 

  5. K. I. Romanova, S. V. Bogatkov, T. D. Sokolova, Yu. F. Malina, and B. V. Unkovskii, Reakts. Sposobnost' Organ. Soedin., 9, 93 (1972).

    Google Scholar 

  6. B. V. Unkovskii, Yu. F. Malina, T. D. Sokolova, S. I. Gavrilova, K. I. Romanova, and Yu. V. Kolosov, Khim. Geterotsikl. Soedin., 1056 (1973).

  7. B. V. Unkovskii, T. D. Sokolova, Yu. F. Malina, and K. I. Romanova, Khim. Geterotsikl. Soedin., 1659 (1973).

  8. T. D. Sokolova, S. V. Bogatkov, Yu. F. Malina, B. V. Unkovskii, and E. M. Cherkasova, Reakts. Sposobnost' Organ. Soedin., 6, 610 (1969).

    Google Scholar 

  9. R. W. Taft, E. Price, I. Tox, I. C. Lewis, K. K. Andersen, and G. T. Davis, J. Am. Chem. Soc., 85, 709, 3146 (1963).

    Google Scholar 

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Authors and Affiliations

  1. M. V. Lomonosov Moscow Institute of Fine-Chemical Technology, USSR

    B. V. Unkovskii, K. I. Romanova, T. D. Sokolova, S. V. Bogatkov & Yu. F. Malina

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  1. B. V. Unkovskii
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  2. K. I. Romanova
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  3. T. D. Sokolova
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  4. S. V. Bogatkov
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  5. Yu. F. Malina
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 89–93, January, 1975.

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Unkovskii, B.V., Romanova, K.I., Sokolova, T.D. et al. Basicities of stereoisomeric derivatives of piperidine and the stereopolar effect. Chem Heterocycl Compd 12, 81–85 (1976). https://doi.org/10.1007/BF00473919

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  • DOI: https://doi.org/10.1007/BF00473919

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