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

Chem. J. Chinese Universities ›› 2011, Vol. 32 ›› Issue (3): 694.

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

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

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.

Abstract

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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CHEN Dong-Dong, DING Chang-Hua, HOU Xue-Long*, DAI Li-Xin. Ring-opening Reaction of Aziridines with α-Carbanion of Oximes[J]. Chem. J. Chinese Universities, 2011, 32(3): 694.

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

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