Chemiluminescence-promoted oxidation of alkyl enol ethers by NHPI under mild conditions and in the dark

T. E. Anderson, Alexander A. Andia, K. A. Woerpel

Research output: Contribution to journalArticlepeer-review

Abstract

The hydroperoxidation of alkyl enol ethers using N-hydroxyphthalimide and molecular oxygen occurred in the absence of catalyst, initiator, or light. The reaction proceeds through a radical mechanism that is initiated by N-hydroxyphthalimide-promoted autoxidation of the enol ether substrate. The resulting dioxetane products decompose in a chemiluminescent reaction that allows for photochemical activation of N-hydroxyphthalimide in the absence of other light sources.

Original languageEnglish (US)
Article number131874
JournalTetrahedron
Volume82
DOIs
StatePublished - Feb 26 2021

Keywords

  • Autoxidation
  • Chemiluminescence
  • Dark
  • Enol ether
  • NHPI
  • Oxidation
  • Radical

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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