Lithium Alkylamide-Catalyzed Addition Reaction of Alkylamines to Vinyl Monomers. III. Addition Reaction of p-Substituted Benzylamines to Styrene and Divinylbenzenes

Article abstract of DOI:10.1246/bcsj.65.1109

The lithium alkylamide-catalyzed addition reaction of p-substituted benzyamines with m- and p-divinylbenzene was examined in order to synthesize new styrene derivatives.Though divinylbenzene possesses two vinyl groups, 1:1 adducts, the N-(p-substituted benzyl)vinylphenethylamines (6, 8) were found to be prepared selectively.The reaction with styrene was also examined as a model reaction.From kinetic studies, the Hammett ρ values for the addition reaction of p-substituted benzylamines to the styrene, m-divinylbenzene and p-divinylbenzene, were -0.72, -0.67, and -1.1, respectively, at 50 deg C.