Arene oxidation with malonoyl peroxides

Andrei Dragan, Tomasz M. Kubczyk, Julian H. Rowley, Stephen Sproules, Nicholas C. O. Tomkinson

Research output: Contribution to journalArticle

24 Citations (Scopus)
33 Downloads (Pure)

Abstract

Malonoyl peroxide 7, prepared in a single step from the commercially available diacid, is an effective reagent for the oxidation of aromatics. Reaction of an arene with peroxide 7 at room temperature leads to the corresponding protected phenol which can be unmasked by aminolysis. An ionic mechanism consistent with the experimental findings and supported by isotopic labeling, Hammett analysis, EPR investigations, and reactivity profile studies is proposed.

Original languageEnglish
Pages (from-to)2618-2621
Number of pages4
JournalOrganic Letters
Volume17
Issue number11
Early online date12 May 2015
DOIs
Publication statusPublished - 5 Jun 2015

Keywords

  • malonoyl peroxide 7
  • diacid
  • aminolysis

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