167421-34-3Relevant academic research and scientific papers
Reactions of nitrile ylids with olefins gem-substituted with withdrawing groups
Perrocheau, Jacques,Danion-Bougot, Renee,Carrie, Robert
, p. 973 - 985 (2007/10/02)
In this study of 1,3-dipolar cycloadditions of nitrile ylids to olefin gem-substituted with withdrawing groups we have attempted to bring out the factors governing the diastereoselectivity of the reaction.Extensive studies have been made with allylic dipoles but few with propargyl dipoles.These reactions lead to stable pyrrol-1-ines in good yields. The adducts have been epimerized and, according to the method of generation of nitrile ylids, the isomerization of the dipoles or the dipolarophiles may occur. These facts have complicated the determination of the kinetic products.Owing to these difficulties, no interpretation of the results with perturbation theory has been attempted. - Keywords: stereochemistry / cycloaddition / 1,3-dipole / nitrile ylid / 1H-azirine / pyrrol-1-ine
