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.

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.
• Public URL: https://durham-repository.worktribe.com/output/1565854