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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
Article

Abstract

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.

Keywords

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.

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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

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