Lithium Alkylamide-Catalyzed Addition Reaction of Alkylamines to Vinyl Monomers. III. Addition Reaction of<i>p</i>-Substituted Benzylamines to Styrene and Divinylbenzenes
作者:Hiroshi Hamana、Fuminori Iwasaki、Hiroyoshi Nagashima、Kazuhisa Hattori、Tokio Hagiwara、Tadashi Narita
DOI:10.1246/bcsj.65.1109
日期:1992.4
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 p 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 °C.
研究了烷基酰胺锂催化的对取代苄胺与间二乙烯基苯和对二乙烯基苯的加成反应,以合成新的苯乙烯衍生物。尽管二乙烯基苯具有两个乙烯基,但1:1加合物,N-(对位取代的苄基)乙烯基苯乙胺(6, 8)被发现是选择性制备的。还检查了与苯乙烯的反应作为模型反应。根据动力学研究,对取代苄胺与苯乙烯、间二乙烯基苯和对二乙烯基苯的加成反应的 Hammett p 值在 50 °C 下分别为 -0.72、-0.67 和 -1.1。