Hydrolytic stability of hydrazones and oximes

Abstract

(Chemical Equation Presented) Watching C 'n' N: Hydrazones and oximes are common conjugates but are labile to hydrolysis. The hydrolytic stabilities of isostructural hydrazones and one oxime were determined at pD 5.0-9.0. The rate constant for the acid-catalyzed hydrolysis of the oxime was nearly 10 3-fold lower than those for simple hydrazones, and a trialkylhydrazonium ion (formed after condensation) was even more stable than the oxime. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.