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

Boris Aleksandrovich Trofimov 1
Boris Aleksandrovich Trofimov
,  , 
Igor Alekseevich Ushakov 1
Igor Alekseevich Ushakov
, 
Andrei Valer'evich Afonin 1
Andrei Valer'evich Afonin
, 
Elena Yur'evna Schmidt 1
Elena Yur'evna Schmidt
, 
Albina Ivanovna Mikhaleva 1
Albina Ivanovna Mikhaleva
10.1016/j.mencom.2011.03.016
Published 2011-03-10
Communication , Volume 21, Issue 2, 103-105
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Trofimov B. A. et al. Stereospecific protonation of pyrrole-2-carboxaldehyde Z-oximes as a result of through-space cation stabilization with oxime hydroxyl // Mendeleev Communications. 2011. Vol. 21. No. 2. pp. 103-105.
GOST all authors (up to 50) Copy
Trofimov B. A., Ivanov A. V., Ushakov I. A., Afonin A. V., Schmidt E. Y., Mikhaleva A. I. Stereospecific protonation of pyrrole-2-carboxaldehyde Z-oximes as a result of through-space cation stabilization with oxime hydroxyl // Mendeleev Communications. 2011. Vol. 21. No. 2. pp. 103-105.
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TY - JOUR
DO - 10.1016/j.mencom.2011.03.016
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2011.03.016
TI - Stereospecific protonation of pyrrole-2-carboxaldehyde Z-oximes as a result of through-space cation stabilization with oxime hydroxyl
T2 - Mendeleev Communications
AU - Trofimov, Boris Aleksandrovich
AU - Ivanov, Andrey Viktorovich
AU - Ushakov, Igor Alekseevich
AU - Afonin, Andrei Valer'evich
AU - Schmidt, Elena Yur'evna
AU - Mikhaleva, Albina Ivanovna
PY - 2011
DA - 2011/03/10
PB - Mendeleev Communications
SP - 103-105
IS - 2
VL - 21
ER -
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@article{2011_Trofimov,
author = {Boris Aleksandrovich Trofimov and Andrey Viktorovich Ivanov and Igor Alekseevich Ushakov and Andrei Valer'evich Afonin and Elena Yur'evna Schmidt and Albina Ivanovna Mikhaleva},
title = {Stereospecific protonation of pyrrole-2-carboxaldehyde Z-oximes as a result of through-space cation stabilization with oxime hydroxyl},
journal = {Mendeleev Communications},
year = {2011},
volume = {21},
publisher = {Mendeleev Communications},
month = {Mar},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2011.03.016},
number = {2},
pages = {103--105},
doi = {10.1016/j.mencom.2011.03.016}
}
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Cite this
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Trofimov, Boris Aleksandrovich, et al. “Stereospecific protonation of pyrrole-2-carboxaldehyde Z-oximes as a result of through-space cation stabilization with oxime hydroxyl.” Mendeleev Communications, vol. 21, no. 2, Mar. 2011, pp. 103-105. https://mendcomm.colab.ws/publications/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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