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.

m-Terphenyl Ethers, a New Hydroxy Protecting Group Cleavable under Reductive Electron Trasfer Reaction Conditions / Azzena, Ugo Gavino; Sarah, Mocci; Pisano, Luisa. - In: SYNTHESIS. - ISSN 0039-7881. - (2011), pp. 1575-1580. [10.1055/s-0030-1259997]

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

AZZENA, Ugo Gavino;PISANO, Luisa
2011

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.
m-Terphenyl Ethers, a New Hydroxy Protecting Group Cleavable under Reductive Electron Trasfer Reaction Conditions / Azzena, Ugo Gavino; Sarah, Mocci; Pisano, Luisa. - In: SYNTHESIS. - ISSN 0039-7881. - (2011), pp. 1575-1580. [10.1055/s-0030-1259997]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11388/86681
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