Abstract
Both the kinetics and the products for the hydrolysis of 2,3,3-triethyloxaziridine in aqueous acid at 25 °C are reported. The reaction is subject to general acid or base catalysis in acetic acid buffers, but in aqueous perchloric acid, the acid catalysis is slight with the rate reaching an unusually sharp maximum in ca. 0.9M HClO4 and then decreasing at higher acidities. Comparison with 2-[αα′-2H2]ethyl-3,3-diethyloxaziridine reveals a substantial primary deuterium isotope effect at low acidities (k0H/k0Dca. 2.7) which steadily decreases to become negligible in 6.68M HClO4. The variation in kinetic parameters relates to a change in the reaction products. In ca. 1M HClO4 the major products are diethyl ketone and acetaldehyde, but N-ethylhydroxylamine is formed at the expense of acetaldehyde as the acidity increases.
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