1312175-89-5Relevant academic research and scientific papers
Bergman cyclization of fluorinated benzo-fused enediynes to naphthalene derivatives: Syntheses and structures
Kane, Christopher M.,Meyers, Tiffany B.,Yu, Xin,Gerken, Michael,Etzkorn, Markus
, p. 2969 - 2980 (2011)
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. Fluorinated naphthalene derivatives were obtained from a series of di- and tetrafluorinated benzo-fused enediyne precursors, readily available by Sonogashira cross-coupling. The crystal structures of six fluorinated benzo-enediynes and of three fluorinated naphthalenes show how acombination of non-covalent arene-(fluoro)arene interactions, hydrogen bonding and crystal packing effects impact the molecular structures in the solid state and, ultimately, lead to very different packing arrangements.
