高等学校化学学报

高等学校化学学报 ›› 2011, Vol. 32 ›› Issue (3): 694.

• 研究论文 • 上一篇    下一篇

肟醚碳负离子对氮杂环丙烷的开环反应

陈冬冬,丁昌华,侯雪龙,戴立信   

  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
  • 收稿日期:2010-10-25 修回日期:2010-12-14 出版日期:2011-03-10 发布日期:2011-02-23
  • 通讯作者: 侯雪龙 E-mail:xlhou@mail.sioc.ac.cn
  • 基金资助:

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

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

CHEN Dong-Dong, DING Chang-Hua, HOU Xue-Long*, DAI Li-Xin   

  1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences,  Shanghai 200032, China
  • Received:2010-10-25 Revised:2010-12-14 Online:2011-03-10 Published:2011-02-23
  • Contact: HOU Xue-Long E-mail:xlhou@mail.sioc.ac.cn
  • Supported by:

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

PDF (PC)

被引次数

6

摘要： 苯乙酮肟醚α碳负离子在添加 HMPA 的条件下，顺利实现了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以对部分氮杂环丙烷开环。反应中 HMPA 起到对锂离子的络合作用，可以在一定程度上增加碳负离子的亲核性。

关键词: 肟醚, 氮杂环丙烷, 开环反应, 碳负离子

Abstract: 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 unstabilized 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.

Key words: oxime, aziridine, ring-opening, carbanion

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