Skip to main content
SpringerLink
Log in

Reduction of disubstituted acetylenes under conditions of organotantalum and organoniobium synthesis

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

Reactions of dialkyl-substituted acetylenes with 4 equiv. of TaCl5 or NbCl5 in toluene in the presence of stoichiometric amounts of magnesium metal regioselectively gave p-tolyl-disubstituted alkanes. Dec-5-yne reacted with the TaCl5—M system (M = Zn, Fe, Sm, Al, Mn) in toluene to selectively afford 1-(dec-5-yl)-4-methylbenzene in 79–90% yields. Effects of the aromatic solvents on the selectivity of the reaction of dec-5-yne with the TaCl5—Mg system were studied.

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. Y. Kataoka, Doctoral dissertation, Kyoto University, Kyoto, 1992, 161 pp.; DOI: https://doi.org/10.11501/3061161.

  2. Y. Kataoka, J. Miyai, K. Oshima, K. Takai, K. Utimoto, J. Org. Chem., 1992, 57, 1973; DOI: https://doi.org/10.1021/jo00033a015.

    Article  CAS  Google Scholar 

  3. K. Takai, Y. Kataoka, K. Utimoto, J. Org. Chem., 1990, 55, 1707; DOI: https://doi.org/10.1021/jo00293a008.

    Article  CAS  Google Scholar 

  4. F. A. Cotton, W. T. Hall, Inorg. Chem., 1981, 19, 2352; DOI: https://doi.org/10.1021/ic50210a034.

    Article  Google Scholar 

  5. F. A. Cotton, W. J. Roth, Inorg. Chim. Acta, 1984, 85, 17; DOI: https://doi.org/10.1016/S0020-1693(00)81020-8.

    Article  CAS  Google Scholar 

  6. F. A. Cotton, J. Lu, J. Inorg. Chem., 1995, 34, 2639; DOI: https://doi.org/10.1021/ic00114a023.

    Article  CAS  Google Scholar 

  7. Y. Kataoka, K. Takai, K. Oshima, K. Utimoto, Tetrahedron Lett., 1990, 31, 365; DOI: https://doi.org/10.1016/S0040-4039(00)94556-8.

    Article  CAS  Google Scholar 

  8. F. A. Cotton, W. T. Hall, K. J. Cann, F. J. Karol, Macromolecules, 1981, 14, 233; DOI: https://doi.org/10.1021/ma50003a001.

    Article  CAS  Google Scholar 

  9. R. N. Kadikova, A. M. Gabdullin, O. S. Mozgovoi, U. M. Dzhemilev, Molecules, 2021, 26, 3722; DOI: https://doi.org/10.3390/molecules26123722.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  10. V. I. Bykov, B. A. Belyaev, T. A. Butenko, Kinet. Catal., 2018, 49, 688; DOI: https://doi.org/10.1134/S0023158418050026.

    Article  Google Scholar 

  11. V. I. Bykov, B. A. Belyaev, Kinet. Catal., 2021, 62, 328; DOI: https://doi.org/10.1134/S0023158421020026.

    Article  CAS  Google Scholar 

  12. K. D. Parker, M. D. Fryzuk, Organometallics, 2015, 34, 2037; DOI: https://doi.org/10.1021/om5010385.

    Article  CAS  Google Scholar 

  13. F. A. Cotton, J. Lu, Inorg. Chem., 1995, 34, 2639; DOI: https://doi.org/10.1021/ic00114a023.

    Article  CAS  Google Scholar 

  14. E. Pérez-Guevara, J. M. G. Molinillo, M. J. Franco, E. J. Martinez de la Ossa, J. Frontela, J. Lázaro, Pet. Chem., 2020, 60, 810; DOI: https://doi.org/10.1134/s0965544120070129.

    Article  Google Scholar 

  15. F. Fairbrother, J. F. Nixon, H. Prophet, J. Less-Common Metals, 1965, 9, 434; DOI: https://doi.org/10.1016/0022-5088(65)90127-X.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Petrochemistry and Catalysis, Ufa Federal Research Center, Russian Academy of Sciences, 141 prosp. Oktyabrya, 450075, Ufa, Bashkortostan, Russian Federation

    A. M. Gabdullin, R. N. Kadikova & I. R. Ramazanov

Authors
  1. A. M. Gabdullin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. R. N. Kadikova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. I. R. Ramazanov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to R. N. Kadikova.

Additional information

This work was financially supported by the Russian Foundation for Basic Research (Project No. 20-33-90274). Recrystallization and drying of tantalum(V) chloride15 and drying of the solvent (toluene) were performed in the framework of the State Tasks of the Ministry of Science and Higher Education of the Russian Federation (FMRS-2022-0076 and FMRS-2022-0075).

No human or animal subjects were used in this research.

The authors declare no competing interests.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 5, pp. 1166–1170, May, 2023.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Gabdullin, A.M., Kadikova, R.N. & Ramazanov, I.R. Reduction of disubstituted acetylenes under conditions of organotantalum and organoniobium synthesis. Russ Chem Bull 72, 1166–1170 (2023). https://doi.org/10.1007/s11172-023-3885-z

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-023-3885-z

Key words

Search

Navigation