Syntheses of Trifluoroethylidene Substituted N-Benzoyl Aziridines

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

(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, Wei^a; Huang, Yangen ^a; Qing, Fengling^*,a,b

(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

Abstract

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

Cite this article

Wu, Wei^a; Huang, Yangen ^a; Qing, Fengling^*,a,b. Syntheses of Trifluoroethylidene Substituted N-Benzoyl Aziridines[J]. Chin. J. Org. Chem., 2009, 29(08): 1249-1253.

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三氟亚乙基取代的N-苯甲酰基氮杂环丙烷的合成

Syntheses of Trifluoroethylidene Substituted N-Benzoyl Aziridines

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