Skip to main content
Log in

Three component reactions of enamines, O,O-dialkyldithiophosphoric acids, and electrophiles

  • Full Article
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

The product of addition of O, O-dialkyldithiophosphoric acid to enamine reacted with the third reaction component of electrophilic nature, for instance, acetyl chloride, α-bromo ether, or sulfenyl bromide. The reaction involving sulfenyl bromide gave the product of reduction of the C—Hal bond of iminium salt and bis(dialkoxythiophosphorylthio) disulfide. This experimentally confirmed the occurrence of the reaction between 2-halo-substituted ald- or ketimines with thio acids via enamine intermediates.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. D. Purdela, R. Vîlceanu, Chimia compuşilor organici ai fos-forului şi ai acizilor lui [Chemistry of Organophosphorus Compounds], Editura Academiei R. S. Romania, Bucharest 1965, 539 p. (in Romanian).

  2. É. E. Nifant´ev, Khimiya fosfororganicheskikh soedinenii [Chemistry of Organophosphorus Compounds], Izd-vo Moscow State University, Moscow, 1971, 351 pp. (in Russian).

    Google Scholar 

  3. D. E. C. Corbridge, Phosphorus: Chemistry, Biochemistry and Technology, Elsevier Sci. Publ., Amsterdam—New York, 2nd ed., 1980, 560 pp.

    Google Scholar 

  4. R. A. Cherkasov, Stroenie ditiokislot fosfora i ikh reaktsion-naya sposobnost´ v reaktsiyakh pricoedineniya [Structure of Phosphorous Dithio Acids and their Reactivity in Addition Reactions], in Stroenie i reaktsionnaya sposobnost´ orga-nicheskikh soedinenii [Structure and Reactivity of Organic Compounds], Nauka, Moscow, 1978, 202 pp. (in Russian).

    Google Scholar 

  5. A. N. Pudovik, I. V. Gur´yanova, É. A. Ishmaeva, Reaktsii i metody issledovaniya organicheskikh soedinenii [Reactions and Evaluation of Organic Compounds], Eds B. A. Kazanskii, I. L. Knunyants, M. M. Shemyakin, N. N. Mel´nikova, Khimiya, Moscow, 1968, Vol. 19, 848 pp. (in Russian).

  6. I. V. Konovalova, L. A. Burnaeva, Reaktsiya Pudovika [The Pudovik Reaction], Izd-vo KGU, Kazan´, 1991, 146 pp. (in Russian).

    Google Scholar 

  7. A. N. Pudovik, M. K. Sergeeva, Zh. Obshch. Khim. [Russ. J. Gen. Chem.], 1955, 25, 1759 (in Russian).

    CAS  Google Scholar 

  8. A. N. Pudovik, M. G. Zimin, Pure Appl. Chem., 1980, 52, 989.

    Article  CAS  Google Scholar 

  9. M. G. Zimin, N. G. Zabirov, R. A. Cherkasov, A. N. Pudovik, Zh. Obshch. Khim. [Russ. J. Gen. Chem.], 1978, 48, 1020 (in Russian).

    CAS  Google Scholar 

  10. M. G. Zimin, N. G. Zabirov, R. A. Cherkasov, A. N. Pudovik, Zh. Obshch. Khim. [Russ. J. Gen. Chem.], 1980, 50, 1458 (in Russian).

    CAS  Google Scholar 

  11. M. B. Gazizov, N. G. Aksenov, O. G. Sinyashin, Tetrahedron Lett., 2015, 56, 4993; DOI: 10.1016/j.tetlet.2015.07.010.

    Article  CAS  Google Scholar 

  12. M. B. Gazizov, R. A. Khairullin, A. I. Perina, A. A. Minnikhanova, N. G. Aksenov, O. I. Gnezdilov, A. V. Il´yasov, Kh. R. Khayarov, Russ. J. Gen. Chem., 2016, 86, 499.

    Article  CAS  Google Scholar 

  13. M. B. Gazizov, R. A. Khairullin, Yu. S. Kirillina, N. Yu. Bashkirtseva, K. S. Gazizova, S. Yu. Ivanova, in Advances in Chemistry Research, Ed. J. C. Taylor, Nova Sci. Publ., New York, 2017, Vol. 41, p. 1.

    Google Scholar 

  14. M. B. Gazizov, R. A. Khairullin, Yu. S. Kirillina, S. Yu. Ivanova, Kh. R. Khayarov, O. D. Khairullina, Russ. Chem. Bull., 2018, 67, 2241.

    Article  CAS  Google Scholar 

  15. M. B. Gazizov, R. A. Khairullin, N. G. Aksenov, Yu. S. Kirillina, A. Yu. Bandikova, Russ. Chem. Bull., 2016, 65, 1119.

    Article  CAS  Google Scholar 

  16. M. B. Gazizov, R. A. Khairullin, N. G. Aksenov, Tetrahedron Lett., 2016, 57, 272; DOI: 10.1016/j.tetlet.2015.11.095.

    Article  CAS  Google Scholar 

  17. M. I. Kabachnik, T. A. Mastryukova, Russ. Chem. Bull., 1954, 3, 369; DOI: 10.1007/BF01167812.

    Article  Google Scholar 

  18. V. A. Al´fonsov, D. A. Pudovik, R. Z. Musin, V. N. Nazmutdinova, Yu. Ya. Efremov, É. S. Batyeva, A. N. Pudovik, Zh. Obshch. Khim. [Russ. J. Gen. Chem.], 1988, 58, 1734 (in Russian).

    Google Scholar 

  19. N. G. Zabirov, F. M. Shamsevaleev, R. A. Cherkasov, Zh. Obshch. Khim. [Russ. J. Gen. Chem.], 1991, 61, 616 (in Russian).

    CAS  Google Scholar 

  20. H. G. Corkins, L. Storace, D. Weinberger, E. Osgood, S. Lowery, Phosphorus Sulfur Relat. Elem., 1981, 10, 133; DOI: 10.1080/03086648108077494.

    Article  CAS  Google Scholar 

  21. A. G. Liakumovich, V. Kh. Kadirova, N. A. Mukmenova, S. V. Bukharova, Zh. Obshch. Khim. [Russ. J. Gen. Chem.], 1991, 61, 260 (in Russian).

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to M. B. Gazizov.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 0110–0113, January, 2020.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Gazizov, M.B., Khairullin, R.A., Kirillina, Y.S. et al. Three component reactions of enamines, O,O-dialkyldithiophosphoric acids, and electrophiles. Russ Chem Bull 69, 110–113 (2020). https://doi.org/10.1007/s11172-020-2730-x

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-020-2730-x

Key words

Navigation