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Chemistry of Hexafluorobicyclo[1.1.0]butane: A Computational Study

  作者 LEMAL DAVID M  
  选自 期刊  Journal of Organic Chemistry;  卷期  2010年75-19;  页码  6411-6415  
  关联知识点  
 

[摘要]Despite its very weak central C C bond, the yet-unknown hexafluorobicyclobutane is predicted to be quite robust. Unlike the parent hydrocarbon, which undergoes thermal rearrangement to butadiene, the perfluoro compound will yield hexafluorocyclobutene upon heating. The fluorobicyclobutane will react under mild conditions with a variety of reagents, in particular with certain alkenes in a new type of concerted transformation. This "fluorohomoene" reaction is shown to be a pseudopericyclic process, as is condensation of the bicyclobutane with water. Whereas the carbene 3-butenylidene rearranges primarily to butadiene, its perfluoro counterpart is predicted to be an efficient precursor for hexafluorobicyclobutane.

 
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