81428-90-2Relevant academic research and scientific papers
Michael Reaction, VI. Effect of Carbonyl Compounds on the Sterechemistry and Mechanism of the Reaction
Viteva, Lilia Z.,Stefanovsky, Yuri N.
, p. 181 - 190 (2007/10/02)
The equilibrium stereochemical result of the two-step Michael reaction between phenylacetic acid dialkylamides and methyl cinnamate or cinnamic acid dialkylamides is affected by the neutral carbonyl compounds taking part in the systhesis.This effect is explained by breakdown of the intramolecular chelate structure of the reaction adduct and appearance of an open metal form with isomeric partitioning close to that of the neutral adduct.This is further supported by the increased electroconductivity of the reaction mixtures.A chelate mechanism for the reaction in nonpolar medium is postulated which is in good agreement with the low stereoselectivity under kinetic conditions as well as with the effect of the polarity of the solvent on the kinetic stereochemical result.Keywords: Mechanism; Michael reaction; Stereochemistry.
