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Synthesis 2004(5): 722-734  
DOI: 10.1055/s-2004-815969
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© Georg Thieme Verlag Stuttgart · New York

Synthesis of 1-Phosphono-2-aza-1,3-dienes and Scope of their Aziridination

Bart Vanderhoydonck, Christian V. Stevens*
Department of Organic Chemistry, Faculty of Agricultural and Applied Biological Sciences, Ghent University, Coupure Links 653, 9000 Ghent, Belgium
Fax: +32(9)2646243; e-Mail: Chris.Stevens@UGent.be;
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Publication History

Received 22 December 2003
Publication Date:
24 February 2004 (online)

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Abstract

Several 1-phosphono-2-aza-1,3-dienes 14 and 1-aryl-1-phosphono-2-aza-1,3-dienes 15-17 were prepared by 1,4-dehydrochlorination of the corresponding diethyl [(2-chloro-1-alkylidene)amino]methylphosphonates 10-13. 1-Phosphono-2-aza-1,3-dienes 14 react smoothly with diazomethane to give 2-phosphono-1-vinylaziridines 18. The synthesis of 2-ethoxycarbonyl-3-phosphono-1-vinylaziridines 19 was performed using ethyl diazo­acetate (EDA) in the presence of ytterbium(III) triflate as a catalyst. 2-Phosphono-3-(trimethylsilyl)aziridines 20 were prepared from phosphonoazadienes 14 by treatment with (trimethylsilyl)di­azomethane under reflux. 1-Aryl-1-phosphono-2-aza-1,3-dienes are not susceptible to aziridination under these conditions.

Key words

2-azadienes - 1-phosphono-2-azadienes - phosphonoaziridines - diazo compounds - imines - Lewis acids - lanthanides