Polarity reversal induced by electrochemically generated thiazol-2-ylidenes: The Stetter reaction
| Autor: | Isabella Chiarotto, Achille Inesi, Giovanni Sotgiu, Monica Orsini |
|---|---|
| Přispěvatelé: | I., Chiarotto, M., Orsini, Sotgiu, Giovanni, A., Inesi |
| Rok vydání: | 2010 |
| Předmět: |
chemistry.chemical_classification
Electrochemical reduction General Chemical Engineering Stetter reaction Aldehyde Umpolung chemistry.chemical_compound chemistry stetter reaction n-heterocyclic carbene thiazolium salt electrochemical reduction stetter reaction thiazolium salt electrochemical reduction n-heterocyclic carbene N-Heterocyclic carbene Ionic liquid Electrochemistry Michael reaction Organic chemistry Reactivity (chemistry) Solvent effects Carbene |
| Zdroj: | Electrochimica Acta. 55:3511-3517 |
| ISSN: | 0013-4686 |
| Popis: | The inversion of the normal reactivity (umpolung) of aldehydes has been induced via N-heterocyclic carbenes (NHCs) thiazol-2-ylidenes 2a or 3a, generated by simple electrolyses of solutions containing thiazolium salt 2 or 3. Accordingly, 1,4-dicarbonyl compounds have been obtained, in mild conditions and in moderate to very high yields, via 1,4-addition of the Breslow intermediates to the suitable Michael acceptor. The procedure has been performed in classical organic solvents (VOCs) as well as in room temperature ionic liquids (RTILs). The different reactivity of aliphatic aldehydes vs the one of aromatic and heteroaromatic aldehydes has been emphasized. |
| Databáze: | OpenAIRE |
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