Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2007, Issue 20, Pages 3365-3368Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200700244
Keywords
acetal; hydrolysis; cleavage reactions; kinetics; reaction mechanism
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A series of sterically similar five- and six-membered ring cyclic diol-derived ketone acetals have been prepared and their rates of acid-catalysed hydrolysis examined. The rates of hydrolysis are substantially affected by acetal ring conformational stereoelectronic effects and resonance effects depending upon the substituents on the parent ketone; an A1 mechanism of hydrolysis explains the observed effects. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007).
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