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Site‐selective Oxidative Dearomatization of Phenols and Naphthols into ortho ‐Quinols or Epoxy ortho ‐Quinols using Oxone as the Source of Dimethyldioxirane
Author(s) -
CabreraAfonso María J.,
Carreño M. Carmen,
Urbano Antonio
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201900660
Subject(s) - dimethyldioxirane , chemistry , phenols , acetone , epoxy , organic chemistry , oxidative phosphorylation , ether , reactivity (psychology) , biochemistry , medicine , alternative medicine , pathology
A novel reactivity of dimethyldioxirane, generated in situ from Oxone and acetone, with substituted phenols and naphthols is reported. This methodology allowed the synthesis of ortho ‐quinols or epoxy ortho ‐quinols from a site‐selective oxidative dearomatization process, with good yields under very mild conditions. A short total synthesis of natural product lacinilene C methyl ether is also described using this process as the key step.