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The effects of ring size and substituents on the rates of acid-catalysed hydrolysis of five- and six-membered ring cyclic ketone acetals

Knowles, J.P.; Whiting, A.

Authors

J.P. Knowles



Abstract

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.

Citation

Knowles, J., & Whiting, A. (2007). The effects of ring size and substituents on the rates of acid-catalysed hydrolysis of five- and six-membered ring cyclic ketone acetals. European Journal of Organic Chemistry, 2007(20), 3365-3368. https://doi.org/10.1002/ejoc.200700244

Journal Article Type Article
Publication Date Jul 1, 2007
Deposit Date Jan 23, 2008
Journal European Journal of Organic Chemistry
Print ISSN 1434-193X
Electronic ISSN 1099-0690
Publisher Wiley
Peer Reviewed Peer Reviewed
Volume 2007
Issue 20
Pages 3365-3368
DOI https://doi.org/10.1002/ejoc.200700244
Keywords Acetal, Hydrolysis, Cleavage reactions, Kinetics, Reaction mechanism.