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Studies on the Chemical Constituents of Rutaceous Plants. Part LXIX. Cesium Fluoride-Mediated Claisen Rearrangement of Aryl Propargyl Ether. Exclusive Formation of 2-Methylarylfuran and Its Availability as a Masked Salicylaldehyde.
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1992
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EngineeringBotanyOrganic ChemistryChemistryStepwise OxidationStereoselective SynthesisPhytochemicalPharmacologyAsymmetric CatalysisNatural Product SynthesisEnantioselective SynthesisBiomolecular EngineeringChemical ConstituentsClaisen RearrangementNatural SciencesPart LxixPhytochemistryPhenol GroupSynthetic ChemistryRutaceous Plants
Claisen rearrangement of an aryl propargyl ether in the presence of CsF led to exclusive formation of 2-methylarylfuran in excellent yield. The result of a precise examination of the rearrangement is described. Satisfactory transformation of the 2-methylarylfuran to a salicylaldehyde derivative was achieved by stepwise oxidation. This combination of reactions serves as a useful method for regioselective introduction of a C1 unit at the ortho position of a phenol group.