Voltammetric behavior of β-phosphonylated nitroxide and its application to electrocatalytic oxidation of alcohol

Yoshitomo Kashiwagi, Takuya Nishimura, Jun ichi Anzai

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)

Abstract

N-tert-Butyl-N-[1-diethylphosphono-(2,2-dimethylpropyl)]nitroxide (DEPN) as β-phosphonylated nitroxide was prepared using tert-butylamine, pivalaldehyde and phosphonic acid diethyl ether as starting materials. This nitroxide revealed a reversible redox peak in cyclic voltammetry at +0.81 V versus Ag/AgCl, and showed electrocatalysis for the oxidation of alcohol. A preparative electrocatalytic oxidation of 4-methylbenzyl alcohol on the nitroxide yielded 98% 4-methylbenzaldehyde by 10 h of electrolysis. The current efficiency, turnover number and pseudo-first-order kinetic constant of the reaction were 96.5%, 39 and 0.95 × 10-5 s-1, respectively.

Original languageEnglish
Pages (from-to)1317-1320
Number of pages4
JournalElectrochimica Acta
Volume47
Issue number8
DOIs
Publication statusPublished - 2002 Feb 1

Keywords

  • Alcohol
  • Electrocatalytic oxidation
  • Mediator
  • β-Phosphonylated nitroxide

ASJC Scopus subject areas

  • Chemical Engineering(all)
  • Electrochemistry

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