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Title: Relative tendency of carbonyl compounds to form enamines
Author: Sánchez Pérez, Daniel
Bastida, David
Burés Amat, Jordi
Isart Garriga, Carles
Pineda, Oriol
Vilarrasa i Llorens, Jaume
Keywords: Reaccions d'addició
Compostos carbonílics
Espectroscòpia de ressonància magnètica nuclear
Addition reactions
Carbonyl compounds
Nuclear magnetic resonance spectroscopy
Issue Date: 6-Jan-2012
Publisher: American Chemical Society
Abstract: Equilibria between carbonyl compounds and their enamines (from O-TBDPS-derived prolinol) have been examined by NMR spectroscopy in DMSO-d 6. By comparing the exchange reactions between pairs (enamine A + carbonyl B → carbonyl A + enamine B), a quite general scale of the tendency of carbonyl groups to form enamines has been established. Aldehydes quickly give enamines that are relatively more stable than those of ketones, but there are exceptions to this expected rule; for example, 1,3-dihydroxyacetone acetals or 3,5-dioxacyclohexanones (2-phenyl-1,3-dioxan-5-one and 2,2-dimethyl-1,3- dioxan-5-one) show a greater tendency to afford enamines than many α-substituted aldehydes
Note: Versió postprint del document publicat a:
It is part of: Organic Letters, 2012, vol. 14, num. 2, p. 536-539
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ISSN: 1523-7060
Appears in Collections:Articles publicats en revistes (Química Inorgànica i Orgànica)

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