1355016-96-4Relevant articles and documents
Transfer of 1-alkenyl groups between secondary amines. Relative stability and reactivity of enamines from popular organocatalysts
Carneros, Hector,Sanchez, Dani,Vilarrasa, Jaume
, p. 2900 - 2903 (2014/06/23)
Enamines from 3-methylbutanal and several Pro- and Phe-derived secondary amines were prepared in DMSO-d6, CD3CN, and CDCl 3. For the first time, the relative thermodynamic stabilities of these and other enamines were compared, and rapid exchanges of 1-alkenyl groups were demonstrated. Competition experiments showed that the most favored enamines (without significant steric inhibition of resonance) react more rapidly with electrophiles.
Relative tendency of carbonyl compounds to form enamines
Sanchez, Dani,Bastida, David,Bures, Jordi,Isart, Carles,Pineda, Oriol,Vilarrasa, Jaume
supporting information; experimental part, p. 536 - 539 (2012/03/26)
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.
