Department of Chemistry, St. John's University, 8000 Utopia Parkway, Jamaica, New York 11439 USA
Abstract:
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.