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Conversion of 1,4-Diketones into para-Disubstituted Benzenes

  作者 ZIFFLE VINCENT E; CHENG PING; CLIVE DERRICK L J  
  选自 期刊  Journal of Organic Chemistry;  卷期  2010年75-23;  页码  8024-8038  
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[摘要]Reaction of acetylides with aldehydes to form but-2-yne-1,4-diols, followed by triple bond reduction and oxidation of the hydroxyl groups, gives 1,4-diketones; these react with vinyllithium, and, the resulting diols undergo ring-closing metathesis to form 2-cyclohexene-1,4-diols. Dehydration, usually by acid treatment, then gives benzenes carrying substituents in a 1,4 relationship. Use of substituted vinyllithiums provides further substitution on the final benzene rings. The method can be applied to the synthesis of C5-aryl carbohydrates.

 
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