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Acid-Induced Rearrangement Reactions of alpha-Hydroxy-1,3-dithianes

  作者 KROHN KARSTEN; CLUDIUSBRANDT STEPHAN  
  选自 期刊  Synthesis;  卷期  2010年-8;  页码  1344-1348  
  关联知识点  
 

[摘要]Secondary benzylic or aliphatic alpha-hydroxydithianes 1a-c rearrange to alpha-thioketones when treated with acid. Related tertiary alcohols 1d-g eliminate to dithioketene ketals (e. g., 2d), which are ring-opened to thiols in some cases (1e, 1f). Allylic alpha-hydroxydithianes 1h and 1i form the thioesters 2h and 2i (homologation), and the tertiary alcohols 1j and 1k undergo deoxygenation to 2j and 2k.

 
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