ORGN 421 |
| 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 CCl4). 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.
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Heterocycles and Aromatics, Molecular Recognition and Self Assembly
8:00 PM-10:00 PM, Tuesday, April 8, 2008 Morial Convention Center -- Hall A, Poster
Division of Organic Chemistry |
