Superacidic Activation of α,β-Unsaturated Amides and Their Electrophilic Reactions Full article
| Journal |
European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690 |
||
|---|---|---|---|
| Output data | Year: 2004, Number: 19, Pages: 4039-4047 Pages count : 9 DOI: 10.1002/ejoc.200400313 | ||
| Tags | Electrophilic reactions, Superacids, Superelectrophilic activation | ||
| Authors |
|
||
| Affiliations |
|
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.
Cite:
Koltunov K.Y.
, Walspurger S.
, Sommer J.
Superacidic Activation of α,β-Unsaturated Amides and Their Electrophilic Reactions
European Journal of Organic Chemistry. 2004. N19. P.4039-4047. DOI: 10.1002/ejoc.200400313 WOS Scopus РИНЦ ANCAN OpenAlex
Superacidic Activation of α,β-Unsaturated Amides and Their Electrophilic Reactions
European Journal of Organic Chemistry. 2004. N19. P.4039-4047. DOI: 10.1002/ejoc.200400313 WOS Scopus РИНЦ ANCAN OpenAlex
Dates:
| Submitted: | May 5, 2004 |
| Published online: | Sep 16, 2004 |
| Published print: | Oct 1, 2004 |
Identifiers:
| Web of science: | WOS:000224422600013 |
| Scopus: | 2-s2.0-5444246866 |
| Elibrary: | 14666598 |
| Chemical Abstracts: | 2004:868559 |
| Chemical Abstracts (print): | 142:6117 |
| OpenAlex: | W2155494963 |