m-Terphenyl Ethers, a New Hydroxy Protecting Group Cleavable under Reductive Single Electron Transfer Reaction Conditions

Abstract

m-Terphenyl ethers and, to a lesser extent, 2,6-dimeth­oxyphenyl ethers, were tested as protected hydroxy derivatives under a variety of reaction conditions. These ethers underwent regioselective cleavage of the aromatic C(1)-O bond under reductive SET reaction conditions using alkali metals in tetrahydrofuran at room temperature. This deprotective procedure was efficiently realized in the presence of several other functional groups, including an acetal, a phenyl alkyl ether, an unprotected alcohol, and carbon-carbon double and triple bonds. Furthermore, m-terphenyl ethers proved stable under different reaction conditions, including acidic hydrolysis and formation and/or employment of different organometallic reagents.

alcohols - electron transfer - protecting groups - reduction - sodium

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