Chemistry of Heterocyclic Compounds

, Volume 54, Issue 2, pp 205–208 | Cite as

Epoxidation of 4,5-dialkyl-2,3-dihydro-1Н-phosphole 1-oxides

  • Vladimir A. D’yakonov
  • Rina A. Agliullina
  • Alevtina L. Makhamatkhanova
  • Tatyana V. Tyumkina
  • Usein M. Dzhemilev

A method was developed for the synthesis of 1,5-dialkyl(cycloalkyl,phenyl)-2-phenyl-6-oxa-2-phosphabicyclo[3.1.0]hexane 2-oxides from alkynes, involving the epoxidation of unsaturated cyclic organophosphorus compounds with m-chloroperbenzoic acid. The organophosphorus compounds were obtained by a reaction sequence consisting of catalytic cycloalumination of symmetrical acetylenes with triethylaluminum in the presence of bis(cyclopentadienyl)zirconium(IV) dichloride catalyst leading to the formation of 2,3-disubstituted aluminacyclopent-2-enes and in situ reaction of the latter with dichlorophenylphosphine.


aluminacyclopentenes 2,3-dihydrophospholes epoxyphospholanes heterocyclic compounds organoaluminum compounds zirconocene dichloride cycloalumination epoxidation metal complex catalysis 


This work received financial support from the Russian Foundation for Basic Research (project 16-33-00193) and grant of the President of the Russian Federation (NSh-5240.2018.3). The structural studies were performed with the use of Collective Usage Center “Agidel” at the Institute of Petrochemistry and Catalysis, Russian Academy of Sciences.

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  1. 1.
    Mitsuya, H.; Weinhold, K. J.; Furman, P. A.; St. Clair, M. H.; Lehrman, S. N.; Gallo, R. C.; Bolognesi, D.; Barry, D. W.; Broder, S. Proc. Natl. Acad. Sci. USA 1985, 82, 7096.Google Scholar
  2. 2.
    Mccormick, J. B.; Mitchell, S. W.; Getchell, J. P.; Hicks, D. R. Lancet 1984, 324, 1367.CrossRefGoogle Scholar
  3. 3.
    Secrist III, J. A.; Riggs, R. M.; Tiwari, K. N.; Montgomery, J. A. J. Med. Chem. 1992, 35, 533.CrossRefGoogle Scholar
  4. 4.
    Shealy Y. F.; Clayton, J. D. J. Am. Chem. Soc. 1966, 88, 3885.CrossRefGoogle Scholar
  5. 5.
    Seto, H.; Kuzuyama,T. Nat. Prod. Rep. 1999, 16, 589.Google Scholar
  6. 6.
    Hendlin, D.; Stapley, D. O.; Jackson, M.; Wallick, H.; Miller, A. K.; Wolf, F. J.; Miller, T. W.; Chaiet, L.; Kahan, F. M.; Foltz, E. L.; Woodruff, H. B.; Hernandez, S.; Mochales, S. Science 1969, 166, 122.CrossRefGoogle Scholar
  7. 7.
    Yamaoka, M.; Yamashita, M.; Yamada, M.; Fujie, M.; Kiyofuji, K.; Ozaki, N.; Asai, K.; Niimi, T.; Suyama, T.; Yamashita, J.; Sawada, A.; Makita, R.; Sugiyama, M.; Toda, M.; Nakamura, S.; Ohnishi, K. Pure Appl. Chem. 2012, 84, 37.CrossRefGoogle Scholar
  8. 8.
    D'yakonov, V. A.; Makhamatkhanova, A. L.; Agliullina, R. A.; Tyumkina, T. V.; Dzhemilev, U. M. Tetrahedron Lett. 2014, 55, 3913.CrossRefGoogle Scholar
  9. 9.
    D'yakonov, V. A.; Makhamatkhanova, A. L.; Dilmukhametova, L. K.; Agliullina, R. A.; Tyumkina, T. V.; Dzhemilev, U. M. Organometallics 2015, 34, 221.CrossRefGoogle Scholar
  10. 10.
    D'yakonov, V. A.; Makhamatkhanova, A. L.; Agliullina, R. A.; Dilmukhametova, L. K.; Tyumkina, T. V.; Dzhemilev, U. M. Beilstein J. Org. Chem. 2016, 12, 406.Google Scholar
  11. 11.
    Yamashita, M.; Reddy, V. K.; Rao, L. N.; Haritha, B.; Maeda, M.; Suzuki, K.; Totsuka, H.; Takahashi, M.; Oshikawa, T. Tetrahedron Lett. 2003, 44, 2339.CrossRefGoogle Scholar
  12. 12.
    Ito, S.; Yamashita, M.; Niimi, T.; Fujie, M.; Reddy, V. K.; Totsuka, H.; Haritha, B.; Maddali, K.; Nakamura, S.; Asai, K.; Suyama, T.; Yamashita, J.; Iguchi, Y.; Yu, G.; Oshikawa, T. Heterocycl. Commun. 2009, 15, 23.Google Scholar
  13. 13.
    Hussain, H.; Al-Harrasi, A.; Green, I. R.; Ahmed, I.; Abbas, G.; Rehman, N. U. RSC Adv. 2014, 4, 12882.CrossRefGoogle Scholar
  14. 14.
    Quin, L. D.; Wu, X.-P. Heteroat. Chem. 1991, 2, 359.Google Scholar
  15. 15.
    Quin, L. D.; Symmes, C.; Middlemas, E. D.; Lawson, H. F. J. Org. Chem. 1980, 45, 4688.CrossRefGoogle Scholar
  16. 16.
    Reddy, V. K.; Haritha, B.; Oshikawa, T.; Yamashita, M. Tetrahedron Lett. 2004, 45, 2851.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • Vladimir A. D’yakonov
    • 1
  • Rina A. Agliullina
    • 1
  • Alevtina L. Makhamatkhanova
    • 1
  • Tatyana V. Tyumkina
    • 1
  • Usein M. Dzhemilev
    • 1
  1. 1.Institute of Petrochemistry and CatalysisRussian Academy of SciencesUfaRussia

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