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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 Enamines Espectroscòpia de ressonància magnètica nuclear Addition reactions Carbonyl compounds Enamines 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: https://doi.org/10.1021/ol203157s |
It is part of: | Organic Letters, 2012, vol. 14, num. 2, p. 536-539 |
URI: | http://hdl.handle.net/2445/158643 |
Related resource: | https://doi.org/10.1021/ol203157s |
ISSN: | 1523-7060 |
Appears in Collections: | Articles publicats en revistes (Química Inorgànica i Orgànica) |
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