Russian Journal of Organic Chemistry

, Volume 52, Issue 4, pp 533–537 | Cite as

Reaction of 1-[2-(vinyloxy)ethyl]-1H-pyrroles with trifluoroacetic anhydride

  • E. Kh. Sadykov
  • N. A. Lobanova
  • V. K. Stankevich


Chemo- and stereoselectivity of the reaction of 1-[2-(vinyloxy)ethyl]-1H-pyrroles with trifluoroacetic anhydride have been studied. The reaction with an equimolar amount of trifluoroacetic anhydride chemoselectively involves the free α-position of the pyrrole ring with formation of the corresponding α-trifluoroacetylpyrroles. In the reaction with 2 equiv of trifluoroacetic anhydride, acylation of both α-position of the pyrrole ring and β-position of the vinyloxy group leads to the formation of 1-(2-{[(1E)-4,4,4-trifluoro-3-oxobut-1-en-1-yl]oxy}ethyl)-2-trifluoroacetyl derivatives with high stereoselectivity.


Pyrrole Vinyl Ether Pyrrole Ring Trifluoroacetyl Trifluoroacetic Anhydride 
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

© Pleiades Publishing, Ltd. 2016

Authors and Affiliations

  • E. Kh. Sadykov
    • 1
  • N. A. Lobanova
    • 1
  • V. K. Stankevich
    • 1
  1. 1.Favorskii Irkutsk Institute of Chemistry, Siberian BranchRussian Academy of SciencesIrkutskRussia

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