volume 2004 issue 19 pages 4039-4047

Superacidic Activation of α,β‐Unsaturated Amides and Their Electrophilic Reactions

Konstantin Yu Koltunov 1
Stéphane Walspurger 1
Jean Sommer 1
1
 
Laboratoire de physico‐chimie des hydrocarbures, UMR 7513, Université L. Pasteur, 4 rue B. Pascal, 67000 Strasbourg, France, Fax: (internat.) + 33‐390241487
Publication typeJournal Article
Publication date2004-10-01
scimago Q2
wos Q2
SJR0.558
CiteScore4.3
Impact factor2.7
ISSN1434193X, 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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GOST Copy
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.
GOST all authors (up to 50) Copy
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.
RIS |
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RIS Copy
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 -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@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}
}
MLA
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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.