Do aziridines require Lewis acids for cleavage with ionic nucleophiles?

Bisai, Alakesh ; Pandey, Ghanshyam ; Pandey, Manoj K. ; Singh, Vinod K. (2003) Do aziridines require Lewis acids for cleavage with ionic nucleophiles? Tetrahedron Letters, 44 (31). pp. 5839-5841. ISSN 0040-4039

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Official URL: http://www.sciencedirect.com/science/article/pii/S...

Related URL: http://dx.doi.org/10.1016/S0040-4039(03)01414-X

Abstract

A variety of activated aziridines were cleaved by sodium azide and sodium cyanide in aqueous acetonitrile at reflux, in the absence of any Lewis acid, to provide ring-opened products in quantitative yields. However, the reaction was sluggish in the ring opening of unactivated aziridines with sodium azide where the yields could be increased by adding 50 mol% CuCl2·2H2O. The reaction was used to synthesize chiral diamines.

Item Type:Article
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ID Code:55363
Deposited On:18 Aug 2011 08:39
Last Modified:18 Aug 2011 08:39

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