Surprising electrooxidation of propargyl alcohol to (Z)-3-(2-propynoxy)-2- propenoic acid at a NiOOH electrode in alkaline medium

Leticia García-Cruz, Jesús Iniesta, Thies Thiemann, Vicente Montiel

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

The electrooxidation of the unsaturated propargyl alcohol has been explored on NiOOH electrodes in alkaline solution. Cyclic voltammetry, chronoamperometry and electrolyses were performed for the electrochemical response of propargyl alcohol. The identification and quantification of the final products from the electrolyses have been carried out. No evidence for the formation of propiolic acid has been found, however, a new product, (Z)-3-(2-propynoxy)-2-propenoic acid, was obtained. The stereochemistry of the product could be ascertained by 1H NMR spectroscopy. A tentative mechanism for the formation of (Z)-3-(2-propynoxy)-2-propenoic acid has been developed.

Original languageEnglish
Pages (from-to)200-202
Number of pages3
JournalElectrochemistry Communications
Volume22
Issue number1
DOIs
Publication statusPublished - Aug 2012

Keywords

  • (Z)-3-(2-propynoxy)-2- propenoic acid
  • Alkyn-1-ols
  • Nickel oxyhydroxide
  • Propargyl alcohol
  • Stereoselectivity

ASJC Scopus subject areas

  • Electrochemistry

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