Skip to main content
SpringerLink
Log in

Reaction of secondary phosphine oxides with acylacetylenes

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

Abstract

Secondary phosphine oxides reacted with 1-alkanoyl-2-phenylacetylenes in chemoselective fashion under mild conditions (20°C, THF) in the absence of a catalyst (diphenylphosphine oxide) or in the presence of potassium hydroxide [bis(2-phenylethyl)phosphine oxide] to give 1-alkyl-1-diphenyl(or 2-phenylethyl)-phosphoryl-3-phenylprop-2-yn-1-ols in up to 96% yield. The reaction of diphenylphosphine oxide with 1-alkanoyl-2-phenylacetylenes in the system KOH-THF (20°C) afforded not only adducts at the carbonyl group but also products of double α,β-addition at the triple bond, 2,3-bis(diphenylphosphoryl)-3-phenylpropan-1-ones.

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

Access this article

Log in via an institution

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. Noyori, R., Ohkuma, T., Kitamura, M., Takaya, H., Sayo, N., Kumobayashi, H., and Akutagawa, S., J. Am. Chem. Soc., 1987, vol. 109, p. 5856.

    Article  CAS  Google Scholar 

  2. Hayashi, M., Takezaki, H., Hashimoto, Y., Takaoki, K., and Saigo, K., Tetrahedron Lett., 1998, vol. 39, p. 7529.

    Article  CAS  Google Scholar 

  3. Tolis, E.I., Vallianatou, K.A., Andreadaki, F.J., and Kostas, I.D., Appl. Organomet. Chem., 2006, vol. 20, p. 335.

    Article  CAS  Google Scholar 

  4. Snee, P.T., Somers, R.C., Nair, G., Zimmer, J.P., Bawendi, M.G., and Nocera, D.G., J. Am. Chem. Soc., 2006, vol. 128, p. 13 320.

    Article  CAS  Google Scholar 

  5. Paine, R.T., Bond, E.M., Parveen, S., Donhart, N., Duesler, E.N., Smith, K.A., and Nöth, H., Inorg. Chem., 2002, vol. 41, p. 444.

    Article  CAS  Google Scholar 

  6. Alguacil, F.J. and Alonso, M., Hydrometallurgy, 2004, vol. 74, p. 157.

    Article  CAS  Google Scholar 

  7. Chan, Z., Yan-Zhao, Y., Tao Z., Jian, H., and Chang-Hong, L., J. Radioanal. Nucl. Chem., 2005, vol. 265, p. 419.

    Article  Google Scholar 

  8. Plotnikova, G.V., Malysheva, S.F., Gusarova, N.K., Khaliullin, A.K., Udilov, V.P., and Kuznetsov, K.L., Zh. Prikl. Khim., 2008, vol. 81, p. 314.

    Google Scholar 

  9. Yin, J., Lin, Y., Cao, X., Yu, G.-A., Tu, H., and Liu, S.H., Dyes Pigm., 2009, vol. 81, p. 152.

    Article  CAS  Google Scholar 

  10. Subhan, M.A., Hasegawa, Y., Suzuki, T., Kaizaki, S., and Shozo, Y., Inorg. Chim. Acta, 2009, vol. 362, p. 136.

    Article  CAS  Google Scholar 

  11. Gusarova, N.K., Arbuzova, S.N., Shaikhudinova, S.I., Kazantseva, T.I., Reutskaya, A.M., Ivanova, N.I., Papernaya, L.K., and Trofimov, B.A., Phosphorus, Sulfur, Silicon Relat. Elem., 2001, vol. 175, p. 163.

    Article  CAS  Google Scholar 

  12. Gusarova, N.K., Ivanova, N.I., Reutskaya, A.M., Arbuzova, S.N., Baikalova, L.V., Deryagina, E.N., Russavskaya, N.V., and Trofimov, B.A., Russ. J. Org. Chem., 2001, vol. 37, p. 1726.

    Article  CAS  Google Scholar 

  13. Ivanova, N.I., Gusarova, N.K., Reutskaya, A.M., Shaikhudinova, S.I., Arbuzova, S.N., and Trofimov, B.A., Russ. J. Gen. Chem., 2003, vol. 73, p. 877.

    Article  CAS  Google Scholar 

  14. Takaku, H., Miyamoto, Y., Asami, S., Shimazaki, M., Yamada, S., Yamamoto, K., Udagawa, N., DeLuca, H.F., and Shimizu, M., Bioorg. Med. Chem., 2008, vol. 16, p. 1796.

    Article  CAS  Google Scholar 

  15. Stockland, R.A., Taylor, R.I., Thompson, L.E., and Patel, P.B., Org. Lett., 2005, vol. 7, p. 851.

    Article  CAS  Google Scholar 

  16. Trofimov, B.A., Sukhov, B.G., Malysheva, S.F., and Gusarova, N.K., Katal. Promst., 2006, p. 18.

  17. Arbuzova, S.N., Gusarova, N.K., and Trofimov, B.A., Arkivoc, 2006, part (v). p. 12.

  18. Kawaguchi, S., Nomoto, A., Sonoda, M., and Ogawa, A., Tetrahedron Lett., 2009, vol. 50, p. 624.

    Article  CAS  Google Scholar 

  19. Glotova, T.E., Dvorko, M.Yu., Arbuzova, S.N., Ushakov, I.A., Verkhoturova, S.I., Gusarova, N.K., and Trofimov, B.A., Lett. Org. Chem., 2007, vol. 4, p. 109.

    Article  CAS  Google Scholar 

  20. Kleiner, H.-J., Justus Liebigs Ann. Chem., 1974, p. 751.

  21. Well, M. and Schmutzler, R., Phosphorus, Sulfur Silicon Relat. Elem., 1992, vol. 72, p. 171.

    Article  CAS  Google Scholar 

  22. Gusarova, N.K., Reutskaya, A.M., Ivanova, N.I., Medvedeva, A.S., Demina, M.M., Novopashin, P.S., Afonin, A.V., Albanov, A.I., and Trofimov B.A., J. Organomet. Chem., 2002, vol. 659, p. 172.

    Article  CAS  Google Scholar 

  23. Ivanova, N.I., Reutskaya, A.M., Gusarova, N.K., Medvedeva, S.A., Afonin, A.V., Ushakov, I.A., Tatarinova, A.A., and Trofimov, B.A., Russ. J. Gen. Chem., 2003, vol. 73, p. 1354.

    Article  CAS  Google Scholar 

  24. Ivanova, N.I., Gusarova, N.K., Nikitina, E.A., Albanov, A.I., Sinegovskaya, L.M., Nikitin, M.V., Konovalova, N.A., and Trofimov, B.A., Phosphorus, Sulfur Silicon Relat. Elem., 2004, vol. 179, p. 7.

    Article  CAS  Google Scholar 

  25. Dvorko, M.Yu., Glotova, T.E., Ushakov, I.A., Gusarova, N.K., and Trofimov, B.A., Russ. J. Org. Chem., 2008, vol. 44, p. 1245.

    Article  CAS  Google Scholar 

  26. Nifant’ev, E.E., Khimiya gidrofosforil’nykh soedinenii (Chemistry of Hydrophosphoryl Compounds), Moscow: Nauka, 1983.

    Google Scholar 

  27. Kormachev, V.V. and Fedoseev, M.S., Preparativnaya khimiya fosfora (Preparative Phosphorus Chemistry), Perm: Ural. Otd. Ross. Akad. Nauk, 1992.

    Google Scholar 

  28. Trofimov, B.A., Gusarova, N.K., Malysheva, S.F., Arbuzova, S.N., Shaikhudinova, S.I., and Sukhov, B.G., Nauka Proizv., 2003, no. 6, p. 10.

  29. Shostakovskii, M.F., Nakhmanovich, A.S., Knutov, V.N., and Klochkova, L.G., Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim., 1968, issue 12, no. 5, p. 104.

Download references

Author information

Authors and Affiliations

  1. Favorskii Irkutsk Institute of Chemistry, Siberian Division, Russian Academy of Sciences, ul. Favorskogo 1, Irkutsk, 664033, Russia

    M. Yu. Dvorko, T. E. Glotova, I. A. Ushakov & N. K. Gusarova

Authors
  1. M. Yu. Dvorko
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. T. E. Glotova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. I. A. Ushakov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. N. K. Gusarova
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to T. E. Glotova.

Additional information

Original Russian Text © M.Yu. Dvorko, T.E. Glotova, I.A. Ushakov, N.K. Gusarova, 2010, published in Zhurnal Organicheskoi Khimii, 2010, Vol. 46, No. 4, pp. 495–500.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Dvorko, M.Y., Glotova, T.E., Ushakov, I.A. et al. Reaction of secondary phosphine oxides with acylacetylenes. Russ J Org Chem 46, 485–490 (2010). https://doi.org/10.1134/S1070428010040056

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428010040056

Keywords

Search

Navigation