Oxidative dearomatization of phenols and anilines via lambda(3)- and lambda(5)-iodane-mediated phenylation and oxygenation

Molecules. 2005 Jan 31;10(1):201-16. doi: 10.3390/10010201.

Abstract

Treatment of 2-methylphenols with chloro(diphenyl)-lambda(3)-iodane led to their regioselective dearomatizing 2-phenylation into cyclohexa-2,4-dienone derivatives via a proposed ligand coupling reaction. In the same vein of investigation, treatment of 2-methylanilines with the lambda(5)-iodane 2-iodoxybenzoic acid IBX reagent led to their regioselective dearomatization into previously undescribed ortho-quinol imines.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aniline Compounds / chemistry*
  • Benzene / chemistry*
  • Bridged Bicyclo Compounds, Heterocyclic / pharmacology
  • Cyclization / drug effects
  • Iodine Compounds / pharmacology*
  • Iodobenzenes / chemistry
  • Iodobenzenes / pharmacology
  • Models, Biological
  • Oxidation-Reduction
  • Oxygen / chemistry*
  • Phenols / chemistry*

Substances

  • Aniline Compounds
  • Bridged Bicyclo Compounds, Heterocyclic
  • Iodine Compounds
  • Iodobenzenes
  • Phenols
  • chloro(diphenyl)-lambda(3)-iodane
  • o-iodoxybenzoic acid
  • Benzene
  • Oxygen