Skip to main content
SpringerLink
Log in

Reactions of tautomeric quaternary phosphonium salts based on triphenylphosphine and 3-phenylpropargyl bromide with nitrogen nucleophiles

  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

Triphenyl(3-phenylprop-1-ynyl)phosphonium bromide (3) was isolated. This compound is a third isomer for the tautomeric system triphenyl(3-phenylpropadienyl)phosphonium bromide (1) ⇌ triphenyl(3-phenylprop-2-ynyl)phosphonium bromide (2). Salts 1 and 2 smoothly react with secondary amines to give adducts with an α,β-double bond, while salt 3 changes to an allene ylide. Addition of phenylhydrazine and triphenyl(phenylethynyl)phosphonium bromide to salts 1 and 2 and addition of dimethylformamide to salt 2 were performed.

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. R. A. Khachatrian, G. A. Mkrtchian, F. S. Kinoian, and M. G. Indzhikian, Arm. Khim. Zh., 1987, 40, 696.

    Google Scholar 

  2. R. A. Khachatrian, G. A. Mkrtchian, F. S. Kinoian, and M. G. Indzhikian, Zh. Obshch. Khim., 1986, 56, 231 [J. Gen. Chem. USSR, 1986, 56 (Engl. Transl.)].

    Google Scholar 

  3. H. Hoffmann and H. Foerster, Tetrahedron Lett., 1964, 17-18, 983.

    Google Scholar 

  4. E. E. Schweiser, S. De Voc Goff, and N. P. Murrey, J. Org. Chem., 1977, 42, 200.

    Google Scholar 

  5. J. D. Applegart and C. M. J. Stiring, J. Chem. Soc., C, 1969, 1904.

  6. E. E. Schweiser and M. A. Galcagno, J. Org. Chem., 1978, 43, 4207.

    Google Scholar 

  7. E. E. Schweiser and S. Hirwe, J. Org. Chem., 1982, 47, 1652.

    Google Scholar 

  8. E. E. Schweiser, J. Org. Chem., 1987, 52, 1810.

    Google Scholar 

  9. E. E. Schweiser and S. De Voc Goff, J. Org. Chem., 1978, 43, 2972.

    Google Scholar 

  10. E. E. Schweiser, S. S. Kim, and S. C. Laban, J. Chem. Soc., C, 1973, 7.

  11. G. Young and W. R. P. Corfild, Synthesis, 1997, 961.

  12. R. A. Khachatrian, G. A. Mkrtchian, and M. G. Indzhikian, Zh. Obshch. Khim., 1987, 57, 293 [J. Gen. Chem. USSR, 1987, 57 (Engl. Transl.)].

    Google Scholar 

  13. R. A. Khachatrian, G. A. Mkrtchian, A. M. Torgomian, and M. G. Indzhikian, Zh. Obshch. Khim., 1993, 63, 2151 [Russ. J. Gen. Chem., 1993, 63 (Engl. Transl.)].

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. National Academy of Sciences of the Republic of Armenia, Institute of Organic Chemistry, 167a ul. Zakhariya Kanakertsi, 375091, Yerevan, Republic of Armenia

    R. A. Khachatrian, S. A. Zalinian, G. B. Bagdasarian, E. A. Sarkisova & M. G. Indzhikian

Authors
  1. R. A. Khachatrian
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. A. Zalinian
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. G. B. Bagdasarian
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. E. A. Sarkisova
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. M. G. Indzhikian
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Khachatrian, R.A., Zalinian, S.A., Bagdasarian, G.B. et al. Reactions of tautomeric quaternary phosphonium salts based on triphenylphosphine and 3-phenylpropargyl bromide with nitrogen nucleophiles. Russian Chemical Bulletin 51, 148–150 (2002). https://doi.org/10.1023/A:1015034402464

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1015034402464

Search

Navigation