Skip to main content
Log in

Alkylation of hetaryl methyl ketones by propargyl bromide under phase-transfer catalysis conditions

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The alkylation of aryl and hetaryl methyl ketones by propargyl bromide using the phase-transfer catalysis system KOH (s)/18-crown-6/benzene is studied. The corresponding C-trialkylated products are selectively obtained in 34–78% yields.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. W. D. Huntsman,The Chemistry of the Carbon-Carbon Triple Bond, S. Patai (ed.), Wiley Interscience, London (1978).

    Google Scholar 

  2. S. I. Miller and J. I. Dickstein,Acc. Chem. Res.,9, 358 (1976).

    CAS  Google Scholar 

  3. E. V. Dehmlow and S. S. Dehmlow,Phase Transfer Catalysis, Third, Revised and Enlarged Edition, VCH Publ., Inc., New York (1993), p. 166.

    Google Scholar 

  4. M. Lissel, B. Neumann, and S. Schmidt,Liebigs Ann. Chem., No. 3, 263 (1987).

    Google Scholar 

  5. E. M. Abele, R. N. Abele, Yu. Yu. Popelis, A. P. Gaukhman, and E. Lukevics,Zh. Org. Khim.,34, 1391 (1998).

    Google Scholar 

  6. E. M. Abele, Yu. Sh. Goldberg, Yu. Yu. Popelis, and M. V. Shymanska,Zh. Org. Khim.,26, 1784 (1990).

    CAS  Google Scholar 

  7. Yu. Goldberg, E. Abele, and M. Shymanska,Synth. Commun.,20, 2741 (1990).

    CAS  Google Scholar 

  8. Yu. Goldberg, E. Abele, and M. Shymanska,Synth. Commun.,21, 557 (1991).

    CAS  Google Scholar 

  9. K. Rubina, Yu. Goldberg, and M. Shymanska,Synth. Commun. 19, 2489 (1989).

    CAS  Google Scholar 

  10. Organic Synthesis, John Wiley & Sons, New York (1932), Vol. 12, p. 62.

Download references

Authors

Additional information

Dedicated to Professor Henk van der Plas on his 70th birthday.

Latvian Institute of Organic Synthesis, Riga LV-1006,

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 495–497, April, 1999.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Abele, E., Abele, R., Popelis, Y. et al. Alkylation of hetaryl methyl ketones by propargyl bromide under phase-transfer catalysis conditions. Chem Heterocycl Compd 35, 436–438 (1999). https://doi.org/10.1007/BF02319330

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02319330

Keywords

Navigation