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Stereochemical features of addition of O- and C-nucleophiles to 5-(Het)aryl-2,3-dicyano-1-ethylpyrazinium salts

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Abstract

Stable σH-adducts of O- and C-nucleophiles were obtained with cations of 5-(het)aryl-2,3-dicyano-1-ethylpyrazinium, and their structure was investigated by X-ray diffraction analysis. Analytical separation was performed of 1,2-dihydropyrazines into individual enantiomers by means of HPLC on columns with chiral sorbents.

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References

  1. Hou, D. and Matsuoka, M., Dyes and Pigments, 1993, vol. 22, p. 57.

    Article  CAS  Google Scholar 

  2. Jaung, J.-Y., Matsuoka, M., and Fukunishi, K., Dyes and Pigments, 1996, vol. 31, p. 141.

    Article  CAS  Google Scholar 

  3. Lee, B.H., Jaung, J.-Y., Jang, S.C., and Yi, S.C., Dyes and Pigments, 2005, vol. 65, p. 159.

    Article  CAS  Google Scholar 

  4. Zimcik, P., Miletin, M., Ponec, J., Kostka, M., and Fiedler, Z., J. Photochem. Photobiol. A: Chem., 2003, vol. 155, p. 127.

    Article  CAS  Google Scholar 

  5. Zimcik, P., Miletin, M., Kostka, M., Schwarz, J., Musil, Z., and Kopecky, K., J. Photochem. Photobiol. A: Chem., 2004, vol. 164, p. 21.

    Article  Google Scholar 

  6. Hou, D., Oshida, A. and Matsuoka, M., J. Heterocycl. Chem., 1993, p. 1571.

  7. Matsuoka, M., J. Heterocycl. Chem., 1993, p. 1571.

  8. Barlin, G.B., The Pyrazines, New York: Wiley-Interscience, 1982.

    Google Scholar 

  9. Hirano, H., Lee, R., and Tada, M., J. Heterocycl. Chem., 1982, p. 1409.

  10. Brach, P.J., Grammatica, S.J., and Ossanna, A.O., Weinberger, L., J. Heterocycl. Chem., 1970, p. 1403.

  11. Popp, F.D., J. Heterocycl. Chem., 1974, p. 79.

  12. Slepukhin, P.A., Rusinov, G.L., Charushin, V.N., Filyakova, V.I., Karpenko, N.S., Krivolapov, D.B., and Litvinov, I.A., Izv. Akad. Nauk, Ser. Khim., 2004, p. 1.

  13. Charushin, V.N., Kazantseva, I.V., Ponizovskii, M.G., Egorova, L.G., Sidorov, E.O., and Chupakhin, O.N., Khim. Geterotsikl. Soedin. 1986, p. 1380.

  14. Charushin, V.N., Ponizovskii, M.G., Chupakhin, O.N., Sidorov, E.O., and Sosonkin, I.M., Khim. Geterotsikl. Soedin., 1985, p. 669.

  15. Chupakhin, O.N., Charushin, V.N., and Chernyshev, A.R., Prog. Nucl. Magn. Res. Spectr., 1988, vol. 20, p. 95.

    Article  Google Scholar 

  16. Egorov, I.N., Zyryanov, G.V., Rusinov, V.L., and Chupakhin, O.N., Usp. Khim., 2005, vol. 74, p. 1176.

    Google Scholar 

  17. Ballini, R., Bosica, G., Fiorini, D., Palmieri, A., and Petrini, M., Chem. Rev., 2005, vol. 105, p. 933.

    Article  CAS  Google Scholar 

  18. Chupakhin, O.N., Zyryanov, G.V., Rusinov, V.L., Krasnov, V.P., Levit, G.L. Korolyova, M.A., and Kodess, M.I., Tetrahedron Lett., 2001, vol. 42, p. 2393.

    Article  CAS  Google Scholar 

  19. Verbitskii, E.V., Rusinov, G.L., Slepukhin, P.A., Matern, A.I., Shvachko, Yu.N., Starichenko, D.V., Charushin, V.N., and Chupakhin, O.N., Izv. Akad. Nauk, Ser. Khim., 2006, p. 2035.

  20. Juang, J.-Y., Matsuoka, M., and Fukunishi, K., Dyes and Pigments, 1998, vol. 40, p. 73.

    Article  Google Scholar 

  21. Tietze, L.-F. and Eicher, T., Reactions and Syntheses in the Organic Chemistry Laboratory, Mill Valley, California: University Science Books, 1989.

    Google Scholar 

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Authors and Affiliations

  1. Postovskii Institute of Organic Synthesis, Ural Division, Russian Academy of Sciences, Yekaterinburg, 620041, Russia

    E. V. Verbitskii, G. L. Rusinov, P. A. Slepukhin, A. N. Grishakov, M. A. Ezhikova, M. I. Kodess & V. N. Charushin

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  1. E. V. Verbitskii
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  2. G. L. Rusinov
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  3. P. A. Slepukhin
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  4. A. N. Grishakov
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  5. M. A. Ezhikova
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  6. M. I. Kodess
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  7. V. N. Charushin
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Correspondence to G. L. Rusinov.

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Dedicated to the Full Member of the Russian Academy of Sciences G.A. Tolstikov on occasion of his 75th anniversary

Original Russian Text © E.V. Verbitskii, G.L. Rusinov, P.A. Slepukhin, A.N. Grishakov, M.A. Ezhikova, M.I. Kodess, V.N. Charushin, 2008, published in Zhurnal Organicheskoi Khimii, 2008, Vol. 44, No. 2, pp. 305–312.

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Verbitskii, E.V., Rusinov, G.L., Slepukhin, P.A. et al. Stereochemical features of addition of O- and C-nucleophiles to 5-(Het)aryl-2,3-dicyano-1-ethylpyrazinium salts. Russ J Org Chem 44, 302–310 (2008). https://doi.org/10.1134/S107042800802019X

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  • DOI: https://doi.org/10.1134/S107042800802019X

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