B. A. Trofimov, A. V. Ivanov, I. A. Ushakov, A. V. Afonin, E. Yu. Schmidt, A. I. Mikhaleva, “Stereospecific protonation of pyrrole-2-carboxaldehyde <i>Z</i>-oximes as a result of through-space cation stabilization with oxime hydroxyl”, Mendeleev Commun., 2011, Volume 21, Issue 2,Pages <nobr>103

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

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.

Language: English

DOI: 10.1016/j.mencom.2011.03.016