Literature DB >> 25614209

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

Angie Garcia1, Douglas A L Otte, Walter A Salamant, Jillian R Sanzone, K A Woerpel.   

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.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  carbocations; carbohydrates; electrostatic effects; hydrolysis; kinetics

Mesh：

Substances：

Year:  2015        PMID： 25614209      PMCID： PMC4480982          DOI： 10.1002/anie.201410043

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  10 in total

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  8 in total

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2.  Participation of alkoxy groups in reactions of acetals: violation of the reactivity/selectivity principle in a Curtin-Hammett kinetic scenario.

Authors:  Angie Garcia; Jillian R Sanzone; K A Woerpel
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  8 in total

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