B. A. Trofimov, A. V. Ivanov, I. A. Ushakov, A. V. Afonin, E. Yu. Schmidt, A. I. Mikhaleva, “Stereospecific protonation of pyrrole-2-carboxaldehyde Z-oximes as a result of through-space cation stabilization with oxime hydroxyl”, Mendeleev Commun., 21:2 (2011), 103

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Mendeleev Communications, 2011, Volume 21, Issue 2, Pages 103–105
DOI: https://doi.org/10.1016/j.mencom.2011.03.016 (Mi mendc2881)

Stereospecific protonation of pyrrole-2-carboxaldehyde Z-oximes as a result of through-space cation stabilization with oxime hydroxyl

B. A. Trofimov, A. V. Ivanov, I. A. Ushakov, A. V. Afonin, E. Yu. Schmidt, A. I. Mikhaleva

A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk, Russian Federation

Full-text PDF (354 kB)

DOI: https://doi.org/10.1016/j.mencom.2011.03.016

Abstract: The protonation of the E/Z mixture of pyrrole-2-carboxaldehyde oxime (CF₃COOH, Et₂O or CDCl₃, room temperature) gives Z-configured pyrrole-2-carboxaldehyde oxime cations exclusively. The NMR (¹H, ¹³C and ¹⁵N) analysis and quantum chemical calculations [B3LYP/6-311G(d,p)] imply the stereospecific through-space stabilization of these cations by the oxime hydroxyl.

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Document Type: Article

Language: English

Citation: B. A. Trofimov, A. V. Ivanov, I. A. Ushakov, A. V. Afonin, E. Yu. Schmidt, A. I. Mikhaleva, “Stereospecific protonation of pyrrole-2-carboxaldehyde Z-oximes as a result of through-space cation stabilization with oxime hydroxyl”, Mendeleev Commun., 21:2 (2011), 103–105

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https://www.mathnet.ru/eng/mendc/v21/i2/p103

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