2015•Angewandte ChemieRequires access

Acceleration of Acetal Hydrolysis by Remote Alkoxy Groups: Evidence for Electrostatic Effects on the Formation of Oxocarbenium Ions

Angie Garcia, Douglas A. L. Otte, Walter A. Salamant, Jillian R. Sanzone, Keith A. Woerpel

Abstract

Abstract In contrast to observations with carbohydrates, experiments with 4‐alkoxy‐substituted acetals indicate that an alkoxy group can accelerate acetal hydrolysis by up to 20‐fold compared to substrates without an alkoxy group. The acceleration of ionization in more flexible acetals can be up to 200‐fold when compensated for inductive effects.

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Key concepts: Oxocarbenium, Alkoxy group, Acetal, Hydrolysis, Chemistry, Ion, Leaving group, Medicinal chemistry