Superacidic Activation of α,β‐Unsaturated Amides and Their Electrophilic Reactions
1
Laboratoire de physico‐chimie des hydrocarbures, UMR 7513, Université L. Pasteur, 4 rue B. Pascal, 67000 Strasbourg, France, Fax: (internat.) + 33‐390241487
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Publication type: Journal Article
Publication date: 2004-10-01
scimago Q2
wos Q2
SJR: 0.558
CiteScore: 4.3
Impact factor: 2.7
ISSN: 1434193X, 10990690
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
The electrophilic reactivity of α,β-unsaturated amides towards weak nucleophiles such as arenes and cyclohexane, initiated either with triflic acid (CF3SO3H) or with excess AlCl3, has been studied. The amides generally condense readily with aromatics in the presence of AlCl3 to give 3-arylpropionamides and related compounds in excellent yields, while some amides also undergo selective ionic hydrogenation with cyclohexane to give saturated amides. The proposed mechanism of these reactions involves dicationic intermediates (superelectrophiles). The direct observation of a dicationic species (by low-temperature NMR) is reported. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
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Koltunov K. Yu., Walspurger S., Sommer J. Superacidic Activation of α,β‐Unsaturated Amides and Their Electrophilic Reactions // European Journal of Organic Chemistry. 2004. Vol. 2004. No. 19. pp. 4039-4047.
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Koltunov K. Yu., Walspurger S., Sommer J. Superacidic Activation of α,β‐Unsaturated Amides and Their Electrophilic Reactions // European Journal of Organic Chemistry. 2004. Vol. 2004. No. 19. pp. 4039-4047.
Cite this
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TY - JOUR
DO - 10.1002/ejoc.200400313
UR - https://doi.org/10.1002/ejoc.200400313
TI - Superacidic Activation of α,β‐Unsaturated Amides and Their Electrophilic Reactions
T2 - European Journal of Organic Chemistry
AU - Koltunov, Konstantin Yu
AU - Walspurger, Stéphane
AU - Sommer, Jean
PY - 2004
DA - 2004/10/01
PB - Wiley
SP - 4039-4047
IS - 19
VL - 2004
SN - 1434-193X
SN - 1099-0690
ER -
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BibTex (up to 50 authors)
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@article{2004_Koltunov,
author = {Konstantin Yu Koltunov and Stéphane Walspurger and Jean Sommer},
title = {Superacidic Activation of α,β‐Unsaturated Amides and Their Electrophilic Reactions},
journal = {European Journal of Organic Chemistry},
year = {2004},
volume = {2004},
publisher = {Wiley},
month = {oct},
url = {https://doi.org/10.1002/ejoc.200400313},
number = {19},
pages = {4039--4047},
doi = {10.1002/ejoc.200400313}
}
Cite this
MLA
Copy
Koltunov, Konstantin Yu., et al. “Superacidic Activation of α,β‐Unsaturated Amides and Their Electrophilic Reactions.” European Journal of Organic Chemistry, vol. 2004, no. 19, Oct. 2004, pp. 4039-4047. https://doi.org/10.1002/ejoc.200400313.