Journal of Organic Chemistry p. 1702 - 1706 (1992)
Update date:2022-08-05
Topics:
Getz, John J.
Prankerd, Richard J.
Sloan, Kenneth B.
A series of O-benzamidomethyl derivatives of phenols was synthesized, and their rates of hydrolysis were investigated.The hydrolyses of the compounds follow pseudo-first-order kinetics resulting in quantitative and rapid regeneration of the phenol.The rates of hydrolysis were shown to be dependent on phenol nucleofugicity as well as the pKa of the amide.The mechanism of hydrolysis apparently involves as elimination of the phenol anion from the conjugate base of the amide (E1cB-like).
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