102714-58-9Relevant academic research and scientific papers
Stereochemical Behavior of Intermediary Compounds in the Amine-Catalyzed Knoevenagel Reaction
Tanikaga, Rikuhei,Konya, Naoto,Hamamura, Kazumasa,Kaji, Aritsune
, p. 3211 - 3216 (2007/10/02)
Treatment of the active methylene compounds and aldehydes with a catalytic amount of a secondary amine produces thermodynamically stable alkenes, and the intermediary amino compounds are isolated.The reaction involves many reversible steps, and the stereochemistry of products is determined in the elimination step from the intermediary compounds via stable planar carbanions, in which the small difference in the steric requirements of two electron-withdrawing groups is effective.Steric and electronic effects in the intermediates sometimes bring about the carbon-carbon bond fission with recovery of active methylene compounds, and these effects prevent the Knoevenagel reaction from occuring.
STEREOCHEMISTRY OF AMINE-CATALYZED KNOEVENAGEL REACTIONS
Tanikaga, Rikuhei,Konya, Naoto,Kaji, Aritsune
, p. 1583 - 1586 (2007/10/02)
The amine-catalyzed Knoevenagel reactions of aldehydes and active methylene compounds containing two activating groups were found to involve many reversible steps, and the diastereomeric intermediary condensation compounds yielded thermodynamically stable products via carbanionic intermediates stablized and sterically affected by two activating groups.
