Trofimov reaction

What is Trofimov reaction?

In 1973, Trofimov was the first to report on a reaction now known as the Trofimov reaction. Trofimov reaction involves the synthesis of 2-substituted, 2,3-, or 2,5-disubstituted pyrroles or N-vinylpyrroles through the reaction of ketoximes and acetylene in a superbasic solution (i.e., MOH / DMSO, M = Li, Na, K).

Trofimov reaction - general reaction scheme
Trofimov reaction

Additionally, 2,3-disubstituted pyrroles can also be produced through the reaction of ketoximes and chloroethene or 1,2-dichloroethane in the presence of KOH or NaOH at high temperatures, which generally yields around 40–50 %. Enamine addition to chloroacrylonitrile also yields 2,3-disubstituted pyrroles, but this method has certain drawbacks when it comes to preparing ketoxime intermediates.

References

Trofimov, B. A.; Atavin, A. S.; Mikhaleva, A. I.; Kalabin, G. A. and Chebotareva, E. G., Zh. Org. Khim., 1973, 9, 2205

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