Effect of distortion on the hydrolytic reactivity of amides. 2. N-Pyramidalization: decomposition of N-benzoylaziridines in aqueous media

H Slebocka-Tilk, RS Brown

Index: Slebocka-Tilk, H.; Brown, R. S. Journal of Organic Chemistry, 1987 , vol. 52, # 5 p. 805 - 808

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Citation Number: 37

Abstract

The decomposition of para-substituted N-benzoylaziridines (H, OCH,, NOz, Br) in buffered aqueous media is studied at 25 OC as a function of pH in order to assess the effect of N- pyramidalization on the hydrolytic reactivity of the amide bond. Overall, the reaction shows three dominant terms: OH-and HzO attack on the neutral form and HzO attack on the protonated form of the amide. In base, the exclusive reaction is rate-limiting and ...