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2012-01-06

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Please use this identifier to cite or link to this item: https://hdl.handle.net/2445/158643

Relative tendency of carbonyl compounds to form enamines

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https://doi.org/10.1021/ol203157s

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

Subject

Reaccions d'addició, Compostos carbonílics, Enamines, Espectroscòpia de ressonància magnètica nuclear

Subject (English)

Addition reactions, Carbonyl compounds, Enamines, Nuclear magnetic resonance spectroscopy

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Articles publicats en revistes (Química Inorgànica i Orgànica)

Citation

SÁNCHEZ PÉREZ, Daniel, et al. Relative tendency of carbonyl compounds to form enamines. Organic Letters. 2012. Vol. 14, num. 2, pags. 536-539. ISSN 1523-7060. [consulted: 13 of June of 2026]. Available at: https://hdl.handle.net/2445/158643

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