The synthesis and crystal structures of halogenated tolans p-X–C6H4–CC–C6F5and p-X–C6F4–CC–C6H5(X = F, Cl, Br, I)
Collings, Jonathan C.; Burke, Jacquelyn M.; Smith, Philip S.; Batsanov, Andrei S.; Howard, Judith A. K.; Marder, Todd B.; Collings Jonathan C.; Department of Chemistry, University of Durham; Burke Jacquelyn M.; Department of Chemistry, University of Durham; Smith Philip S.; Department of Chemistry, University of Durham; Batsanov Andrei S.; Department of Chemistry, University of Durham; Howard Judith A. K.; Department of Chemistry, University of Durham; Marder Todd B.; Department of Chemistry, University of Durham
Журнал:
Organic & Biomolecular Chemistry
Дата:
2004
Аннотация:
A series of halogenated, partially fluorinated tolans of general formula p-Xâ C6H4â C.tbd;Câ C6F5 [X = I (1), Br (2), Cl (3), F (4)] and p-Xâ C6F4â C.tbd;Câ C6H5 [X = I (5), Br (6)] have been prepared via palladium-catalysed Sonogashira cross-coupling, or for X = Cl (7), by nucleophilic aromatic substitution reactions. The single-crystal X-ray structures of 1â 3 and 5â 6 have been determined. The structures reveal that the molecular packing is characterized by either areneâ perfluoroarene interactions (3), or halogenâ halogen interactions (isomorphous 1 and 2), or neither (isomorphous 5 and 6). The structure of 3 represents the first fully determined crystal structure of a compound that contains a halogen atom other than fluorine, in which areneâ perfluoroarene interactions are present.
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