Chin. J. Org. Chem. ›› 2009, Vol. 29 ›› Issue (08): 1249-1253. Previous Articles     Next Articles

Original Articles

三氟亚乙基取代的N-苯甲酰基氮杂环丙烷的合成

吴 伟a ; 黄焰根a; 卿凤翎*,a,b   

  1. (a东华大学化学化工与生物工程学院 上海 201620)
    (b中国科学院上海有机化学研究所有机氟化学重点实验室 上海 200032)
  • 收稿日期:2009-03-22 修回日期:2009-04-29 发布日期:2009-08-30
  • 通讯作者: 卿凤翎

Syntheses of Trifluoroethylidene Substituted N-Benzoyl Aziridines

Wu, Weia; Huang, Yangen a; Qing, Fengling*,a,b   

  1. (a College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai 201620)
    (b Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences,
    Shanghai 200032)
  • Received:2009-03-22 Revised:2009-04-29 Published:2009-08-30
  • Contact: Qing, Fengling

A novel method for preparation of trifluoroethylidene substituted N-benzoyl aziridine compounds was developed. Trifluoromethylated propargyl sulfinamides (1) were converted to trifluoromethylated propergylamine hydrochloride 2 via acidic cleavage of the tert-butanesulfinyl groups. N-Benzoyl-2-trifluoroethylideneaziridines 3a~3c were surprisingly obtained in moderate yields by the ben-zoylation reaction of 2 when using NaOH as base. Aziridines 3d~3e can also be obtained in a one pot process starting from propargyl sulfinamides 1. 3b can undergo ring opening reaction under acidic condition to afford compound 6b. The structures of products 3 and 6 were confirmed by IR, 1H NMR, 19F NMR, MS spectra and elemental analyses.

Key words: aziridine, ring opening reaction, trifluoroethylidene