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Bergman Cyclization of Fluorinated Benzo-Fused Enediynes to Naphthalene Derivatives: Syntheses and Structures

  作者 KANE CHRISTOPHER M; MEYERS TIFFANY B; YU XIN; GERKEN MICHAEL; ETZKORN MARKUS  
  选自 期刊  European Journal of Organic Chemistry;  卷期  2011年-16;  页码  2969-2980  
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[摘要]Fluorinated naphthalene derivatives were prepared by Bergman cyclization of fluorinated benzo-fused enediynes. This route provides access to the aromatic target compounds in a two-step procedure from commercially available precursors, via a Sonogashira cross-coupling and a subsequent, thermally initiated Bergman cyclization. Crystal structures of six fluorinated benzo-enediynes and three fluorinated naphthalene derivatives display significant diversity in their molecular structures and in the crystal packing arrangements. The rather subtle structural change from di- to tetrafluorobenzo-enediynes, as well as the variation in the terminal acetylene subunit led to different non-covalent interactions in the solid state that ultimately govern their crystal structures.

 
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