Hemiacetal Ester Exchanges, Study of Reaction Conditions and Mechanistic Pathway

David Boucher, Jeppe Madsen, Nicolas Caussé, Nadine Pébère, Vincent Ladmiral, Claire Negrell

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Abstract

A range of hemiacetal esters were synthesized by the reaction between carboxylic acids and butyl vinyl ether using n-dodecyl dihydrogen phosphate as catalyst. Specifically, nonanoic, propionic, acrylic, sebacic, and fumaric acids were used as substrates to prepare the corresponding hemiacetalesters. These compounds were used as model molecules to demonstrate the ability of hemiacetal ester functional groups to undergo the exchange reaction in the presence of weak carboxylic acids without any catalyst. Kinetics studies examined the eect of the carboxylic acid concentration on the exchange rate, and revealed that the exchange reaction proceeds through an associative mechanism.
Original languageEnglish
JournalReactions
Volume1
Issue number2
Pages (from-to)89-101
ISSN0953-5640
DOIs
Publication statusPublished - 2020

Keywords

  • Hemiacetal ester
  • Exchange reaction
  • Associative
  • Kinetics

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