Russian Journal of Organic Chemistry

, Volume 40, Issue 11, pp 1633–1637 | Cite as

Nitration of phenylpropiolic acid derivatives in HSO3F and reactions of vinyl type cations formed therefrom

  • P. Yu. Savechenkov
  • A. P. Rudenko
  • A. V. Vasil’ev


Nitration of phenylpropiolic acid derivatives ArC≡CX (X=CN, CO2Me) in HSO3F at −75...−50°C afforded mononitro compounds, for instance, m-O2NC6H4C≡CX. Vinyl type cations generated in HSO3F from methyl 3-arylpropiolates ArC+=CHCO2Me react along two pathways. The first among them results in formation of fluorosulfonates ArC(OSO2F)=CHCO2Me, and the second one after the attack of vinyl cation on the aryl moiety of the substrate affords a dimer that on nitration is converted into a nitro product with conserved triple bond.


Methyl Organic Chemistry Vinyl Acid Derivative Nitration 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    Rudenko, A.P., Vasil’ev, A.V., Savechenkov, P. Yu., Sommer, Zh., Khauas, M., and Val’spurzhe, S., Intermediaty. Sintez protonirovanie i okislenie atsetilenovykh soedinenii: Uchebnoe posobie (Intermediates. Synthesis, Protonation, and Oxidation of Acethylene Compounds: Handbook), no. 2, St. Petersburg, 2003, p. 213.Google Scholar
  2. 2.
    Cavechenkov, P. Yu., Rudenko, A.P., and Vasil’ev, A.V., Zh. Org. Khim., 2004, vol. 40, p. 1106.Google Scholar
  3. 3.
    Olah, G. A. and Spear, R. J., J. Am. Chem. Soc., 1975, p. 1845.Google Scholar
  4. 4.
    Rudenko, A.P., Cavechenkov, P. Yu., and Vasil’ev, A.V., Zh. Org. Khim., 2004, vol. 40, p. 1424.Google Scholar
  5. 5.
    Cavechenkov, P. Yu., Vasil’ev, A.V., and Rudenko, A.P., Zh. Org. Khim., 2004, vol. 40, p. 1329.Google Scholar
  6. 6.
    Skvortsov, Yu.M., Mal’kina, A.G., Volkov, A.N., Trofimov, B.A., Oleinikova, E.B., Kazin, I.V., and Gedymin, V.V, Izv. Akad. Nauk SSSR, Ser. Khim., 1978, p. 872.Google Scholar
  7. 7.
    Yadla, R., Rao, V. S., and Rao, J. M., Indian J. Chem., 1982, 21B, p. 1046.Google Scholar
  8. 8.
    Shchelkunov, A.V. and Ivanova, N.N., Fiziko-khimicheskie konstanty atsetilenovykh soedinenii (Physicochemical Constants of Acethylene Compounds), Alma-Ata: Nauka, 1988, p. 97.Google Scholar

Copyright information

© MAIK “Nauka/Interperiodica” 2004

Authors and Affiliations

  • P. Yu. Savechenkov
    • 1
  • A. P. Rudenko
    • 1
  • A. V. Vasil’ev
    • 1
  1. 1.St. Petersburg State Academy of Forestry EngineeringSt. PetersburgRussia

Personalised recommendations