Regioselective intramolecular oxidation of phenols and anisoles by dioxiranes generated in situ

D. Yang, Man Kin Wong, Z. Yan

Research output: Journal article publicationJournal articleAcademic researchpeer-review

33 Citations (Scopus)

Abstract

A novel method for regioselective oxidation of phenols and anisoles has been developed in which dioxiranes, generated in situ from ketones and Oxone, oxidize phenol derivatives in an intramolecular fashion. A series of ketones with electron-withdrawing groups, such as CF3COOMe, and CH2Cl, were attached to phenols, anisoles, or aryl rings via a C2 or C3 methylene linker. In a homogeneous solvent system of CH3CN and H2O, oxidation of phenol derivatives 1-10 afforded spiro 2-hydroxydienones in 24-55% yields regardless of the presence of other substituents (ortho Me, meta Me or Br) on the aryl ring and the length of the linker. Experimental evidences were provided to support the mechanism that involves a regioselective π bond epoxidation of aryl rings followed by epoxide rearrangement and hemiketal formation.
Original languageEnglish
Pages (from-to)4179-4184
Number of pages6
JournalJournal of Organic Chemistry
Volume65
Issue number13
DOIs
Publication statusPublished - 30 Jun 2000
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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