LITHIUM ALKYLAMIDE-CATALYZED ADDITION-REACTION OF ALKYLAMINES TO VINYL MONOMERS .3. ADDITION-REACTION OF PARA-SUBSTITUTED BENZYLAMINES TO STYRENE AND DIVINYLBENZENES

The lithium alkylamide-catalyzed addition reaction of p-substituted benzylamines 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 rho-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-degrees-C.