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

  作者 AZZENA UGO; MOCCI SARAH; PISANO LUISA  
  选自 期刊  Synthesis;  卷期  2011年-10;  页码  1575-1580  
  关联知识点  
 

[摘要]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.

 
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