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含烯基的烯酮和亚胺的反应

发表时间:2012-04-15  浏览量:1286  下载量:601
全部作者: 王志新,许家喜
作者单位: 北京化工大学理学院,化工资源有效利用国家重点实验室
摘 要: 分类综述了含烯基的烯酮和亚胺的反应。烯基烯酮与亚胺或烯酮与烯基亚胺反应可以生成3-或4-烯基-β-内酰胺,以及5,6-或2,3-二氢-1H-吡啶-2-酮。含有烯基的烯酮与亚胺反应形成的两性离子中间体关环时,既可以通过对旋形成六元环产物二氢-1H-吡啶-2-酮,也可以顺旋关环形成四元环产物β-内酰胺。关环的选择性受位阻效应和电子效应的共同影响。而烯基烯酮与烯基亚胺反应经过3,4-二烯基-β-内酰胺中间体重排生成不饱和的八元环内酰胺衍生物。
关 键 词: 物理有机化学;β-内酰胺;综述;烯基烯酮;烯基亚胺;亚胺;烯酮
Title: Reactions of ketenes and imines with alkenyl substituent(s)
Author: WANG Zhixin, XU Jiaxi
Organization: State Key Laboratory of Chemical Resource Engineering, Faculty of Science, Beijing University of Chemical Technology
Abstract: Reactions of ketenes and imines with alkenyl substituent(s) have been reviewed. Reactions of alkenylketenes and imines or ketenes and alkenylimine produce 3-or 4-alkenyl-β-lactams, and 5,6-or 2,3-dihydro-1H-pyridine-2-ones. In the reactions, imines attack the ketenes to generated zwitterionic intermediates. The formed intermidates with conjugative double bonds can undergo either conrotatory four-membered ring closure to give rise to β-lactams, or disrotatory six-membered ring closure to produce six-membered heterocyclic compounds dihydro-1H-pyridine-2-ones. The selectivity in the ring closure is controlled by both steric hindrance and the electronic effect. Reactions of alkenylketenes and alkenylimines give rise to unstable 3,4-dialkenyl-β-lactams, which further undergo the Cope rearrangement to afford unsaturated eight-membered lactams.
Key words: physical organic chemistry; β-lactam; reviews; alkenylketene; alkenylimine; imine; ketene
发表期数: 2012年4月第7期
引用格式: 王志新,许家喜. 含烯基的烯酮和亚胺的反应[J]. 中国科技论文在线精品论文,2012,5(7):591-601.
 
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