Full characterization and some reactions of 1-(2-adamantyl)-3-(1-adamantyl)aziridin-2-one

被引：2
|
作者：
Lengyel, Istvan [1 ]
Taldone, Tony [1 ]
Lyons, Theresa [1 ]
Cesare, Victor [1 ]
机构：
[1] St Johns Univ, Dept Chem, Jamaica, NY 11439 USA
来源：
JOURNAL OF HETEROCYCLIC CHEMISTRY | 2008年 / 45卷 / 03期
关键词：
D O I：
10.1002/jhet.5570450327
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We found that 1-(2-adamantyl)-3-tert-butylaziridin-2-one (5a) is unstable. It slowly decomposes at room temperature, although detectable by IR spectroscopy (1840 cm(-1) band in CCl(4)). On the other hand, a closely related analogue, 1-(2-adamantyl)-3-(1-adamantyl)aziridin-2-one (5b), is very stable, in concurrence with an earlier report [1]. We fully characterized aziridinone 5b, identified its thermal decomposition products (7 and 8) and reacted it with two aprotic ionic (tBuO(-) and HO(-)) and one protic non-ionic nucleophile (benzylamine). All three products (9b, 10, and 11) result from exclusive cleavage of the lactam, (1-2) bond.
引用
收藏
页码：803 / 810
页数：8
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