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, K. A. Woerpel

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish (US)
Pages (from-to)3061-3064
Number of pages4
JournalAngewandte Chemie - International Edition
Volume54
Issue number10
DOIs
StatePublished - Mar 2 2015

Keywords

  • Carbocations
  • Carbohydrates
  • Electrostatic effects
  • Hydrolysis
  • Kinetics

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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