Skip to main content
SpringerLink
Log in

An unusual reaction of propargylamines with CH2I2 and Et3Al

  • Brief Communications
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

N-{2-[(1-R-Cyclopropyl)methyl]prop-2-enyl}-N,N-dimethylamines were prepared in 80-90% yields by the reaction (5 h, 23-25 C) of propargylamines R-C=C-CH2NMe2 (where R = alkyl, Ph) with a system of reactants CH2I2-Et3Al taken in the molar ratio [propargylamine]: [Et3Al]: [CH2I2] = 1: 6: 6. In the case of phenyl-substituted propargyl- amine, N-({1-[(1-phenylcyclopropyl)methyl]cyclopropyl}methyl)-N,N-dimethylamine is selectively formed in 76% yield upon the elongation of the reaction time to 4 days.

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. J. Salaun, in Small Ring Compounds in Organic Synthesis, Vol. 6, Ed. A. de Meijere, Springer-Verlag, Berlin, 2000.

    Google Scholar 

  2. U. M. Dzhemilev, I. R. Ramazanov, A. G. Ibragimov, L.I. Dyachenko, M. P. Lukyanova, O. M. Nefedov, J. Organomet. Chem., 2001, 636, 91.

    Article  CAS  Google Scholar 

  3. I. R. Ramazanov, M. P. Luk’yanova, A. Z. Sharipova, A. G. Ibragimov, U. M. Dzhemilev, O. M. Nefedov, Izv. Akad. Nauk, Ser. Khim., 2001, 1338 [Russ. Chem. Bull., Int. Ed., 2001, 50, 1406].

    Google Scholar 

  4. I. R. Ramazanov, L. K. Dil’mukhametova, U. M. Dzhemilev, O. M. Nefedov, Izv. Akad. Nauk, Ser. Khim., 2009, 1311 [Russ. Chem. Bull., Int. Ed., 2009, 58, 1311].

  5. I. R. Ramazanov, A. V. Yumagulova, U. M. Dzhemilev, O. M. Nefedov, Tetrahedron Lett., 2009, 50, 4233.

    Article  CAS  Google Scholar 

  6. K. Maruoka, Y. Fukutani, H. Yamamoto, J. Org. Chem., 1985, 50, 4412.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Petroleum Chemistry and Catalysis, Russian Academy of Sciences, 141 prosp. Oktyabrya, 450075, Ufa, Bashkortostan, Russian Federation

    I. R. Ramazanov, A. V. Yaroslavova, L. M. Khalilov & U. M. Dzhemilev

  2. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    O. M. Nefedov

Authors
  1. I. R. Ramazanov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. V. Yaroslavova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. L. M. Khalilov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. U. M. Dzhemilev
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. O. M. Nefedov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to I. R. Ramazanov.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1623–1625, August, 2010.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Ramazanov, I.R., Yaroslavova, A.V., Khalilov, L.M. et al. An unusual reaction of propargylamines with CH2I2 and Et3Al. Russ Chem Bull 59, 1668–1670 (2010). https://doi.org/10.1007/s11172-010-0293-y

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-010-0293-y

Search

Navigation