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.
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.
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|
|Peer Reviewed||Peer Reviewed|
|Keywords||Acetal, Hydrolysis, Cleavage reactions, Kinetics, Reaction mechanism.|