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

✍ Scribed by Christopher M. Kane; Tiffany B. Meyers; Xin Yu; Michael Gerken; Markus Etzkorn

• Publisher: John Wiley and Sons
• Year: 2011
• Tongue: English
• Weight: 954 KB
• Volume: 2011
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.201001747

✦ Synopsis

Abstract

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.