肟醚碳负离子对氮杂环丙烷的开环反应  

Ring-opening Reaction of Aziridines with α-Carbanion of Oximes

作　　者：陈冬冬[1] 丁昌华[1] 侯雪龙[1] 戴立信[1] 

机构地区：[1]中国科学院上海有机化学研究所,金属有机化学国家重点实验室,上海200032

出　　处：《高等学校化学学报》2011年第3期694-699,共6页Chemical Journal of Chinese Universities

基　　金：国家“九七三”计划项目(批准号:2010CB833300);国家自然科学基金(批准号:20872161,20821002,20932008)资助

摘　　要：在添加六甲基膦酰胺(HMPA)的条件下,实现了苯乙酮肟醚α-碳负离子对单取代和环状氮杂环丙烷的开环,取得中等到良好的收率.四氢萘酮肟醚α-碳负离子在该条件下也可对部分氮杂环丙烷进行开环反应.反应中HMPA对锂离子发生络合作用,在一定程度上增加碳负离子的亲核性.Aziridine is a very useful synthetic intermediate in organic synthesis.The ring-opening reaction of aziridine with various heteroatom nucleophiles has received intensive attention by organic chemists.However,the development of using carbon nucleophiles,especially unstablized carbon nucleophiles,falls far behind.In this regard,we reported ring-opening reaction of α-carbanion of acetophenone oxime with aziridines in the presence of HMPA,affording corresponding products in moderate to good yields.Tetralone oxime is also a suitable substrate for some monosubstituted aziridines.This method offers a new example of the ring-opening reaction of carbanion with aziridines.

关 键 词：肟醚 氮杂环丙烷 开环反应 碳负离子 

分 类 号：O621[理学—有机化学]