Skip to main content
SpringerLink
Log in

Alkylation of toluene with dichloromethane in the presence of triisobutylaluminum and perfluorophenylborates

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

Abstract

1H NMR method showed that in systems based on triisobutylaluminum (TIBA) and triphenylcyclopropenylium [Ph3C3]+[B(C6F5)4]–(CPB) or triphenylmethylium [Ph3C]+[B(C6F5)4]–(TB) perfluorophenylborates in a toluene–dichloromethane mixture the Friedel–Crafts process occurs with the formation of ditolylmethane (DTM) accompanied by the complete decomposition of TIBA to form isobutane. 19F NMR spectroscopy showed that the [B(C6F5)4]–anion decomposes in the systems to form B(C6F5)3 and HC6F5. The short-living [AlBu2 i]+ cation formed in the reaction of perfluorophenylborates with TIBA is assumed to be the species initiating the process. It has been shown that CPB is less reactive than TB. The addition of a stoichiometric amount of Ph2CCpFluHfMe2 exerts no effect on the process with the CPB-containing system but inhibits the reaction in the case of TB.

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. S. Prajapati, A. P. Mishra, A. Srivastava, IJPCBS, 2012, 2, 52.

    CAS  Google Scholar 

  2. M. Rueping, B. J. Natchtsheim, Beilstein J. Org. Chem., 2010, 6, No.6.

    Article  Google Scholar 

  3. E. Y.-X. Chen, T. J. Marks, Chem. Rev., 2000, 100, 1391.

    Article  CAS  Google Scholar 

  4. J. Kuwabara, D. Takeuchi, T. Osakada, J. Mol. Catal., 2004, 208, 39.

    Article  CAS  Google Scholar 

  5. K. Song, H. Gao, F. Liu, J. Pan, L. Guo, S. Zai, Q. Wu, Eur. J. Inorg. Chem., 2009, 3016.

    Google Scholar 

  6. P. W. Dyer, J. Fawcett, M. J. Hanton, Organometallics, 2008, 27, 5082.

    Article  CAS  Google Scholar 

  7. S. O. Ojwach, I. A. Guzei, L. L. Benade, S. F. Mapolie, J. Darkwa, Organometallics, 2009, 28, 2127.

    Article  CAS  Google Scholar 

  8. A. Budhai, B. Omondi, S. O. Ojwach, C. Obuah, E. Y. OseiTwumb, J. Darkwa, Catal. Sci. Technol., 2013, 3, 3130.

    Article  CAS  Google Scholar 

  9. I. Vicente, K. Bernardo-Gusmão, M. O. de Souza, R. F. de Souza, J. Braz. Chem. Soc., 2014, 25, 2151.

    CAS  Google Scholar 

  10. V. D. Makhaev, A. N. Galiullin, E. E. Faingol´d, N. M. Bravaya, L. A. Petrova, Russ. Chem. Bull. (Int. Ed.), 2014, 63, 651–656 [Izv. Akad. Nauk, Ser. Khim., 2014, 651–656].

    Article  CAS  Google Scholar 

  11. H. Li, D. C. Neckers, Can. J. Chem., 2003, 81, 758.

    Article  CAS  Google Scholar 

  12. M. Bochmann, Topics Catal., 1999, 7, 9.

    Article  CAS  Google Scholar 

  13. M. Bochmann, M. J. Sarsfield, Organometallics, 1998, 17, 5908.

    Article  CAS  Google Scholar 

  14. Z. Yu, A. V. Korolev, M. J. Heeg, C. P. Winter, Polyhedron, 2002, 21, 1117.

    Article  CAS  Google Scholar 

  15. M. P. D. Mahindaratne, K. Wimalasena, J. Org. Chem., 1998, 63, 2858.

    Article  CAS  Google Scholar 

  16. R. Breslow, H. W. Chang, J. Am. Chem. Soc., 1961, 83, 2367.

    Article  CAS  Google Scholar 

  17. C. Götz, A. Rau, G. Luft, Macromol. Symp., 2002, 178, 93.

    Article  Google Scholar 

  18. C. R. Samanami, M. L. Amadoruge, C. H. Yoder, J. A. Colen, C. E. Moore, A. L. Rheingold, N. F. Materer, C. A. Weinert, Organometallics, 2011, 30, 1046.

    Article  Google Scholar 

  19. R. Ma, M. Chen, M. Zhou, J. Phys. Chem. A, 2009, 113, 12926.

    Article  CAS  Google Scholar 

  20. C. A. Reed, N. L. P. Fackler, K.-C. Kim, D. Stasko, D. R. Evans, J. Am. Chem. Soc., 1999, 121, 6314.

    Article  CAS  Google Scholar 

  21. P. Jutzi, C. Müller, A. Stammler, H.-G. Stammler, Organometallics, 2000, 19, 1442.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Problems of Chemical Physics, Russian Academy of Sciences, 1 prosp. Akad. Semenova, 142432, Chernogolovka, Moscow Region, Russian Federation

    N. M. Bravaya, E. E. Faingol’d, A. N. Galiullin, O. N. Babkina, S. L. Saratovskikh, A. V. Chernyak & V. D. Makhaev

Authors
  1. N. M. Bravaya
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. E. E. Faingol’d
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. N. Galiullin
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. O. N. Babkina
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. S. L. Saratovskikh
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. A. V. Chernyak
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. V. D. Makhaev
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to N. M. Bravaya.

Additional information

Dedicated to Academician of the Russian Academy of Sciences N. S. Zefirov on the occasion of his 80th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 2076–2082, September, 2015.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Bravaya, N.M., Faingol’d, E.E., Galiullin, A.N. et al. Alkylation of toluene with dichloromethane in the presence of triisobutylaluminum and perfluorophenylborates. Russ Chem Bull 64, 2076–2082 (2015). https://doi.org/10.1007/s11172-015-1120-2

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-015-1120-2

Key words

Search

Navigation