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Acceleration of acetal hydrolysis by remote alkoxy groups: evidence for electrostatic effects on the formation of oxocarbenium ions.


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.

SUBMITTER: Garcia A 

PROVIDER: S-EPMC4480982 | biostudies-literature | 2015 Mar

REPOSITORIES: biostudies-literature

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Acceleration of acetal hydrolysis by remote alkoxy groups: evidence for electrostatic effects on the formation of oxocarbenium ions.

Garcia Angie A   Otte Douglas A L DA   Salamant Walter A WA   Sanzone Jillian R JR   Woerpel K A KA  

Angewandte Chemie (International ed. in English) 20150122 10


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. ...[more]

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