The spontaneous hydrolysis of acetals: sensitivity to the leaving group
Abstract
The spontaneous hydrolysis of acetals shows very high sensitivity to the basicity of the leaving group, measured as ρ– 2.7 for the hydrolysis of 2-aryloxytetrahydropyrans. A Brønsted (leaving group) plot for the spontaneous hydrolysis of acetals and acylals of formaldehyde shows similar high sensitivity, and correlates also the rate of the acid catalysed hydrolysis of formaldehyde dimethyl acetal.