Skip to main content
Log in

Chiral Salts of Phosphorus Dithioacids Based on Quinine

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

Reactions of quinine with dithioacids based on (1R)-endo-(+)-fenchol, (1S)-endo-(–)-borneol, and (S)-(–)-menthol have afforded optically active quinine salts. Chiral diquinine salts have been obtained in the reactions of quinine with bisthiophosphonic acids based on triethylene glycol and resorcinol.

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. Arbuzov, B.A., Zh. Ross. Fiz.-Khim. O–va, 1927, vol. 59, nos. 3–4, p.247.

    CAS  Google Scholar 

  2. Arbuzov, B.A. and Mikailov, B.M., Zh. Ross. Fiz.-Khim. O–va, 1929, vol. 61, no. 10, p. 2387.

    Google Scholar 

  3. Arbuzov, B.A., Doctoral (Chem.) Dissertation, Kazan, 1936.

    Google Scholar 

  4. Arbuzov, B.A. and Abramov, W.S., Ber., 1934, vol. 67, no. 11, p. 1942.

    Google Scholar 

  5. Arbuzov, B.A. and Isaeva, Z.G., Zh. Obshch. Khim., 1949, vol. 19, no. 5, p.884.

    Google Scholar 

  6. Arbuzov, B.A., Khimiya i primenenie fosfor-organicheskikh soedinenii (Chemistry and the Use of Organophosphorus Compounds), Moscow: Akad. Nauk SSSR, 1962, p.5.

    Google Scholar 

  7. Zielinska-Blajet, M. and Skarzewski, J., Phosphorus, Sulfur, Silicon, Relat. Elem., 2013, vol. 188, p. 1811. doi 10.1080/10426507.2013.788000

    Article  CAS  Google Scholar 

  8. Gorecki, L., Berlicki, L., Mucha, A., Kafarski, P., Slepokura, K., and Rudzinska-Szostak, E., Chirality, 2012, vol. 24, p. 318. doi 10.1002/chir.22000

    Article  CAS  PubMed  Google Scholar 

  9. Vannoorenberghe, Y. and Buono, G., Tetrahedron Lett., 1988, vol. 29, no. 26, p. 3235. doi 10.1016/0040-4039 (88)85130-X

    Article  CAS  Google Scholar 

  10. Chodkiewicz, W., Jore, D., and Wodzki, W., Tetrahedron Lett., 1979, vol. 20, no. 12, p. 1069. doi 10.1016/S0040-4039(01)87194-X

    Article  Google Scholar 

  11. Mizuta, S., Sadamori, M., Fujimoto, T., and Yamamoto, I., Angew. Chem. Int. Ed., 2003, vol. 42, no. 29, p. 3383. doi 10.1002/anie.200250719

    Article  CAS  Google Scholar 

  12. Chodkiewicz, W., J. Organomet. Chem., 1984, vol. 273, no. 3, p. 55. doi 10.1016/0022-328X(84)80557-4

    Article  Google Scholar 

  13. Mizuta, S., Tsuzuki, T., Fujimoto, T., and Yamamoto, I., Org. Lett., 2005, vol. 7, no.17. 3633. doi 10.1021/ol051129m

    Article  CAS  PubMed  Google Scholar 

  14. Rudzińska-Szostak, E., Górecki Ł., Berlicki Ł., Ślepokura, K., and Mucha, A., Chirality, 2015, vol. 27, no. 10, p. 752. doi 10.1002/chir.22494

    Article  CAS  PubMed  Google Scholar 

  15. Nizamov, I.S., Nikitin, E.N., Batyeva, E.S., Faskhetdinov, R.F., and Cherkasov, R.A., Russ. J. Org. Chem., 2015, vol. 51, no. 6, p. 899. doi 10.1134/S1070428015060147

    Article  CAS  Google Scholar 

  16. Nizamov, I.S., Gabdullina, G.T., Terenzhev, D.A., Nurmukhametov, A.R., Nizamov, I.D., and Cherkasov, R.A., Phosphorus, Sulfur, Silicon, Relat. Elem., 2014, vol. 189, no. 9, p. 1354. doi 10.1080/10426507.2013.860531

    Article  CAS  Google Scholar 

  17. Topics in Phosphorus Chemistry. P31 Nuclear Magnetic Resonance, Grayson, M. and Griffith, E.J., Eds., New York: Wiley and Sons, 1967, vol.5.

  18. Shagidullin, R.R., Chernova, A.V., Vinogradova, V.S., and Mukhametov, F.S., Atlas IK-spektrov fosfor-organicheskikh soedinenii (interpretirovannye spektrogrammy) [Atlas of IR Spectra of Organophosphorus Compounds (Interpreted Spectrograms)], Moscow: Nauka, 1984.

    Google Scholar 

  19. Nizamov, I.S., Gabdullina, G.T., Al’metkina, L.A., Shamilov, R.R., Batyeva, E.S., and Cherkasov, R.A., Russ. J. Gen. Chem., 2012, vol. 82, no. 10, p. 1751. doi 10.1134/S1070363212100209

    Article  CAS  Google Scholar 

  20. Nizamov, I.S., Sofronov, A.V., Almetkina, L.A., Musin, R.Z., and Cherkasov, R.A., Russ. J. Gen. Chem., 2010, vol. 80, no. 8, p. 1722. doi 10.1134/S1070363210080268

    Article  CAS  Google Scholar 

  21. Nizamov, I.S., Gabdullina, G.T., Nizamov, I.D., Nikitin Ye.N., Al’metkina, L.A., and Cherkasov, R.A., Phosphorus, Sulfur, Silicon, Relat. Elem., 2010, vol. 185, no. 4, p. 732. doi 10.1080/10426500902930142

    Article  CAS  Google Scholar 

  22. Nizamov, I.S., Nikitin Ye.N., Almetkina, L.A., Sabirzyanova, G.R., Burilov, A.R., and Pudovik, M.A., J. Sulfur Chem., 2011, vol. 32, no. 5, p. 413. doi 10.1080/17415993.2011.613120

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Dedicated to the 115th anniversary of B.A. Arbuzov’s birth

Original Russian Text © I.S. Nizamov, R.Z. Salikhov, I.D. Nizamov, V.Yu. Yakimov, G.G. Sergeenko, E.S. Batyeva, R.A. Cherkasov, 2018, published in Zhurnal Obshchei Khimii, 2018, Vol. 88, No. 11, pp. 1830–1836.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Nizamov, I.S., Salikhov, R.Z., Nizamov, I.D. et al. Chiral Salts of Phosphorus Dithioacids Based on Quinine. Russ J Gen Chem 88, 2307–2313 (2018). https://doi.org/10.1134/S1070363218110105

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363218110105

Keywords

Navigation