Abstract
The reaction of 4-phenylethynylpyrilium salts with indoles leads to indolylvinylpyrilium derivatives through attack of the β-carbon atom of the triple bond and subsequent intramolecular transfer of a proton from C(in3) of the indole ring to the sp-hybridized carbon atom of the allene group. The structure of 2,6-diphenyl-4-[2′-phenyl-2′-((β-methylindolyl)vinyl]pyriliumperchloratewasdeterminedunequivocallybyx-ray diffraction analysis and the most likely reaction scheme was indicated. The bond length distribution in the pyrilium cation indicates significant delocalization of positive charge.
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For communication 3, see [1]
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1316–1324, October, 1992.
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Koblik, A.V., Murad'yan, L.A., Gridunova, G.V. et al. The ethynyl carbocation. 4. Reaction of 4-phenylethynylpyrylium salts with c-nucleophiles. Chem Heterocycl Compd 28, 1116–1123 (1992). https://doi.org/10.1007/BF00529571
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DOI: https://doi.org/10.1007/BF00529571