Studies on the transformation of azido-group to N-(t-butoxycarbonyl)amino group via Staudinger reaction

被引:19
作者
Afonso, CAM [1 ]
机构
[1] Univ Nova Lisboa, Fac Ciencias & Tecnol, Dept Quim, P-2825 Monte De Caparica, Portugal
关键词
D O I
10.1080/00397919808005719
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
By a simple and direct sequence, treatment of primary azides with tri-n-butylphosphine, followed by addition of di-t-butyl dicarbonate (Boc(2)O) affords, N-(t-Butoxycarbonyl)amines 2 in moderate to good overall yields. For secondary azides the formation of symmetrical disubstituted ureas is a competitive process. Conditions were found which, in the presence of a primary amine, allow for moderate selectivity for the reaction with Boc(2)O.
引用
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页码:261 / 276
页数:16
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