Skip to main content
Log in

Intramolecular P=S and P=N Alkylation. General Method for Synthesizing 1,2-Heteraphosphacyclanes

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Results have been generalized for investigations on the synthesis of 1,2-thiaphosphacyclanes by intramolecular P=S alkylation of ω-haloalkyl substituted compounds of four-coordinated phosphorus with a P=S bond. The method has been extended to nitrogen-containing analogs with a P=N bond. A new general method is proposed for the synthesis of 1,2-thia- and 1,2-azaphosphacyclanes.

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.

Institutional subscriptions

Similar content being viewed by others

REFERENCES

  1. D. G. Hewitt and G. L. Newland, Austral. J. Chem., 30, 579 (1977).

    Google Scholar 

  2. T. Sakai, T. Kodama, T. Fujimoto, K. Ohta, and I. Yamamoto, J. Org. Chem., 59, 7144 (1994).

    Google Scholar 

  3. A. Chaudhry, M. P. J. Harger, P. Shaff, and A. Thomson, J. Chem. Soc., Chem. Commun., 83 (1995).

  4. H. Y. Kleiner, Liebigs Ann. Chem., No. 2, 324 (1980).

    Google Scholar 

  5. M. Aladzheva, O. V. Bykhovskaya, D. I. Lobanov, K. A. Lyssenko, M. Yu. Antipin, T. A. Mastryukova, and M. I. Kabachnik, Mendeleev Commun., 48 (1996).

  6. D. I. Lobanov, I. M. Aladzheva, O. V. Bykhovskaya, P. V. Petrovskii, K. A. Lyssenko, M. Yu. Antipin, T. A. Mastryukova, and M. I. Kabachnik, Phosphorus, Sulfur and Silicon, 128, 165 (1997).

    Google Scholar 

  7. I. M. Aladzheva, O. V. Bykhovskaya, D. I. Lobanov, P. V. Petrovskii, K. A. Lysenko, M. Yu. Antipin, T. A. Mastryukova, and M. I. Kabachnik, Zh. Obshch. Khim., 68, 1421 (1998).

    Google Scholar 

  8. I. M. Aladzheva, I. V. Leont′eva, D. I. Lobanov, O. V. Bykhovskaya, P. V. Petrovskii, K. A. Lysenko, T. A. Mastryukova, and M. I. Kabachnik, Zh. Obshch. Khim., 68, 1417 (1998).

    Google Scholar 

  9. T. A. Mastryukova, I. M. Aladzheva, D. I. Lobanov, O. V. Bykhovskaya, P. V. Petrovskii, K. A. Lyssenko, and M. I. Kabachnik, Phosphorus, Sulfur and Silicon, 144-146, 569 (1999).

    Google Scholar 

  10. O. V. Bykhovskaya, I. M. Aladzheva, D. I. Lobanov, P. V. Petrovskii, K. A. Lysenko, and T. A. Mastryukova, Zh. Obshch. Khim., 71, 393 (2001).

    Google Scholar 

  11. V. Mark, C. H. Dungan, M. M. Crutchfield, and J. R. Van Wazer, Topics in Phosphorus Chemistry, Vol. 5, John Wiley, New York (1967), Chap. 4.

    Google Scholar 

  12. R. E. Valters and W. Flitsch, Ring-Chain Tautomerism, Plenum Press, New York (1985), 278 pp.

    Google Scholar 

  13. S. O. Grim and R. C. Barth, J. Organomet. Chem., 94, 327 (1975).

    Google Scholar 

  14. E. Lindner, G. Funk, and S. Hoehne, Chem. Ber., 114, 2465 (1981).

    Google Scholar 

  15. E. Renoud, R. B. Russell, S. Fortier, S. J. Broun, and M. C. Baird, J. Organomet. Chem., 419, 403 (1991).

    Google Scholar 

  16. C. G. Stuckwisch, J. Org. Chem., 41, 1173 (1976).

    Google Scholar 

  17. L. Odinets, N. M. Vinogradova, O. I. Artyushin, P. V. Petrovskii, K. A. Lyssenko, M. Yu. Antipin, and T. A. Mastryukova, Mendeleev Commun., 158 (1999).

  18. L. Odinets, N. M. Vinogradova, K. A. Lyssenko, P. V. Petrovskii, and T. A. Mastryukova, Heteroatom Chem., 11, 163 (2000).

    Google Scholar 

  19. J. H. Davies, J. D. Downer, and P. Kirby, J. Chem. Soc., C, 245 (1966).

  20. R. B. Wetzel and G. L. Kenyon, J. Org. Chem., 39, 1531 (1974).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Aladzheva, I.M., Bykhovskaya, O.V., Lobanov, D.I. et al. Intramolecular P=S and P=N Alkylation. General Method for Synthesizing 1,2-Heteraphosphacyclanes. Chemistry of Heterocyclic Compounds 38, 95–105 (2002). https://doi.org/10.1023/A:1014815628426

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1014815628426

Navigation