Abstract
The reactions of substituted pyroles with terminal acylacetylenes occur selectively to form 2-(Z/E-2-acylvinyl)pyrroles. When the reactions are performed on the surface of silica gel,C-vinylation is noticeably accelerated to form predominantlyE-isomers. ESR spectroscopy with the use of a spin trap demonstrated the ion-radical character of the process. The structures of the adducts synthesized, which exist asanti-s-cis- andsyn-s-cis-rotomers, were studied by IR, UV, and NMR spectroscopy.
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1562–1567, August, 1999.
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Trofimov, B.A., Stepanova, Z.V., Sobenina, L.N. et al. Pyrroles as C-nucleophiles in reactions with acylacetylenes. Russ Chem Bull 48, 1542–1547 (1999). https://doi.org/10.1007/BF02496409
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DOI: https://doi.org/10.1007/BF02496409