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Synthesis and three-dimensional structures of geometrical isomers of some 4-substitute d 1,2,5-trimethyl-4-acetoxy- and 1,2,5-trimethyl-4-benzoxypiperidines

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Stereoisomers of the corresponding 4-substituted 1,2,5-trimethyl-4-acetoxy- and 1,2,5-trimethyl-4-benzoxypiperidines were obtained by acylation of the geometrical isomers of 1,2, 5-trimethyl-4-piperidol and its 4-ethynyl, 4-ethyl, and 4-phenyl-substituted derivatives. The preferred conformations of the investigated esters were elucidated by means of the PMR and IR spectra.

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Literature cited

  1. I. N. Nazarov, D. V. Sokolov, and V. N. Rakcheeva, Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 80 (1954).

  2. I. N. Nazarov, V. Ya. Raigorodskaya, and V. A. Rudenko, Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 504 (1949).

  3. I. N. Nazarov, I. A. Mokhir, B. V. Unkovskii, and G. S. Gusakova, Zh. Obshch. Khim., 29, 1867 (1959).

    Google Scholar 

  4. I. N. Nazarov, N. S. Prostakov, and N. I. Shvetsov, Zh. Obshch. Khim., 26, 2798 (1956).

    Google Scholar 

  5. V. I. Mamonov, G. G. Dvoryantseva, T. D. Sokolova, É. B. Sysoeva, and B. V. Unkovskii, Zh. Organ. Khim., 6, 1087 (1970).

    Google Scholar 

  6. T. F. Vlasova and Yu. N. Sheinker, Zh. Strukt. Khim., 11., 640 (1970).

    Google Scholar 

  7. I. N. Nazarov, B. V. Unkovskii, and I. A. Mokhir, Zh. Obshch. Khim., 30, 742 (1960).

    Google Scholar 

  8. I. N. Nazarov, N. S. Prostakov, N. N. Mikheeva, and O. A. Shavrygina, Zh. Obshch. Khim., 26, 2812 (1956).

    Google Scholar 

  9. N. N. Bolyard and S. M. McElvain, J. Am. Chem. Soc., 51, 922 (1929).

    Google Scholar 

  10. B. V. Unkovskii, I. A. Mokhir, and E. M. Urinovich, Zh. Obshch. Khim., 33, 1808 (1963).

    Google Scholar 

  11. C. I. Schmidle and R. C. Mansfield, J. Am. Chem. Soc., 77, 5698 (1955).

    Google Scholar 

  12. A. Ziering, L. Berger, S. D. Heineman, and J. Lee, J. Org. Chem., 12, 894 (1947).

    Google Scholar 

  13. D. Hirsch, in: Selected Problems of Stereochemistry [Russian translation], Mir, Moscow (1970), p. 199.

    Google Scholar 

  14. B. I. Ionin and B. A. Ershov, NMR Spectroscopy in Organic Chemistry [in Russian], Khimiya, Leningrad (1967), p. 221.

    Google Scholar 

  15. N. Bhacca and D. Williams, Applications of NMR Spectroscopy in Organic Chemistry [Russian translation], Mir, Moscow (1966), p. 69.

    Google Scholar 

  16. H. Rosenkrantz and S. Skrogström, J. Am. Chem. Soc., 77, 2837 (1955).

    Google Scholar 

  17. R. N. Jones and P. Herling, J. Am. Chem. Soc., 78, 1152 (1956),

    Google Scholar 

  18. O. V. Agashkin, G. S. Litvinenko, D. V. Sokolov, and S. S. Chasnikova, Zh. Obshch. Khim., 31, 862 (1961).

    Google Scholar 

  19. R. J. Ouellette, J. Am. Chem. Soc., 86, 3089 (1964).

    Google Scholar 

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No.1, pp. 50–55, January, 1973.

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Sokolova, T.D., Kolosov, Y.V., Malina, Y.F. et al. Synthesis and three-dimensional structures of geometrical isomers of some 4-substitute d 1,2,5-trimethyl-4-acetoxy- and 1,2,5-trimethyl-4-benzoxypiperidines. Chem Heterocycl Compd 9, 42–46 (1973). https://doi.org/10.1007/BF00476147

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  • DOI: https://doi.org/10.1007/BF00476147

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