Skip to main content
SpringerLink
Log in

Features of the Reaction of (1,2-Dibromoethyl)(diphenyl)phosphine Oxide with CH- and NH-Nucleophiles

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

Abstract

The reaction of (1,2-dibromoethyl)(diphenyl)phosphine oxide with CH-acids (acetylacetone, acetoacetic ester, and malonic ester) in the presence of sodium hydroxide has afforded diphenylphosphoryl-substituted cyclopropanes in high yield. It has been shown that the reaction of (1,2-dibromoethyl)(diphenyl)phosphine oxide with primary arylamines leads to the formation of bis(phosphine oxides), in contrast to alkylamines which lead to phosphoryl-substituted aziridines.

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

Scheme
Scheme
Scheme
Scheme

REFERENCES

  1. Goldberg, A.F.G., O’Connor, N.R., Craig, R.A.II, and Stoltz, B.M., Org. Lett., 2012, vol. 14, p. 5314. https://doi.org/10.1021/ol302494n

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  2. Singh, G.S., Adv. Heterocycl. Chem., 2019, vol. 129, p. 245. https://doi.org/10.1016/bs.aihch.2018.12.003

    Article  CAS  Google Scholar 

  3. Katagiri, T., Takahashi, M., Fujiwara, I., Ihara, H., and Uneyama, K., J. Org. Chem., 1999, vol. 64, p. 7323. https://doi.org/10.1021/jo990207e

    Article  CAS  Google Scholar 

  4. Chu, Z.-Y., Li, N., Liang, D., Li, Z.-H., Zheng, Y.-S., and Liu, J.-K., Tetrahedron Lett., 2018, vol. 59, p. 715. https://doi.org/10.1016/j.tetlet.2018.01.016

    Article  CAS  Google Scholar 

  5. Moonen, K., Laureyn, I., and Stevens, Ch.V., Chem. Rev., 2004, vol. 104, p. 6177. https://doi.org/10.1021/cr030451c

    Article  CAS  PubMed  Google Scholar 

  6. Coleman, J.R.S., Li, J., and Navarro, A., Angew. Chem. Int. Ed., 2001, vol. 40, p. 1736. https://doi.org/10.1002/1521-3773(20010504)40:

    Article  CAS  Google Scholar 

  7. Degennaro, L., Trinchera, P., and Luisi, R., Chem. Rev., 2014, vol. 114, p. 7881. https://doi.org/10.1021/cr400553c

    Article  CAS  PubMed  Google Scholar 

  8. Lorenzini, F., Patrick, B.O., and Sames, B.R., Inorg. Chim. Acta, 2008, vol. 361, p. 3199. https://doi.org/10.1016/j.ca.2007.11.017

    Article  CAS  Google Scholar 

  9. Hu, D.-F., Weng, C.-M., and Hong, F.-E., Organometallics, 2011, vol. 30, p. 1139. https://doi.org/10.1021/om101132t

    Article  CAS  Google Scholar 

  10. Hasegawa, Y., Hieda, R., Nakagawa, T., and Kawai, T., Helv. Chim. Acta, 2009, vol. 92, p. 2238. https://doi.org/10.1002/hlca.200900143

    Article  CAS  Google Scholar 

  11. Gasparyan, G.Ts., Оvakimyan, M.Zh., Poghosyan, A.S., Bichakhchyan, A.S., Derdzyan, L.V., and Panosyan, H.A., Russ. J. Org. Chem., 2022, vol. 58, no. 12, p. 1989. https://doi.org/10.1134/S1070428022120314

    Article  CAS  Google Scholar 

Download references

Funding

This work was supported by ongoing institutional funding. No additional grants to carry out or direct this particular research were obtained.

Author information

Authors and Affiliations

  1. Institute of Organic Chemistry, Scientific Technological Centre for Organic and Pharmaceutical Chemistry, National Academy of Sciences of the Republic of Armenia, 0014, Yerevan, Armenia

    G. Ts. Gasparyan, A. S. Bichakhchyan, L. V. Derdzyan, S. Kh. Avetisyan & А. S. Pogosyan

  2. Molecular Structure Research Center, National Academy of Sciences of the Republic of Armenia, 0014, Yerevan, Armenia

    H. A. Panosyan

Authors
  1. G. Ts. Gasparyan
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. S. Bichakhchyan
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. L. V. Derdzyan
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. S. Kh. Avetisyan
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. H. A. Panosyan
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. А. S. Pogosyan
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. S. Bichakhchyan.

Ethics declarations

Authors declare that they have no conflicts of interest.

Additional information

Publisher's Note. Pleiades Publishing remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Gasparyan, G.T., Bichakhchyan, A.S., Derdzyan, L.V. et al. Features of the Reaction of (1,2-Dibromoethyl)(diphenyl)phosphine Oxide with CH- and NH-Nucleophiles. Russ J Gen Chem 94, 62–65 (2024). https://doi.org/10.1134/S1070363224010055

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363224010055

Keywords:

Search

Navigation