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

✍ Scribed by István Lengyel; Tony Taldone; Theresa Lyons; Victor Cesare

Publisher
Journal of Heterocyclic Chemistry
Year
2008
Tongue
English
Weight
844 KB
Volume
45
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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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 (__t__BuO^−^ 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.

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