European Journal of Organic Chemistry p. 1493 - 1502 (2019)
Update date:2022-08-29
Topics:
Seidel, Pierre
Schwarzer, Anke
Mazik, Monika
9,9-Diethylfluorenes bearing chloromethyl, bromomethyl, and iodomethyl groups in the 2, 4, and 7 positions of the aromatic skeleton were prepared and their solid-state structures determined by single-crystal X-ray diffraction analysis. The prepared fluorenes represent not only valuable starting materials for a wide range of fluorene-based compounds but are also interesting objects for the analysis of the supramolecular motifs in the crystalline state. The X-ray diffraction experiments revealed that the asymmetric unit of each structure contains one molecule, featuring similar conformations, but differ in their modes of non-covalent intermolecular bonding. The crystal structures of the chloromethyl and bromomethyl substituted compounds 1 and 2 are primarily stabilized by Hal···Hal and C–H···Hal contacts, whereas the packing of the iodine substituted analogous compound 3 is influenced by triangular I3 synthons, C–H···π interactions and to a less degree by C–H···I contacts. The manuscript provides information about new synthetic routes, new molecules as well as about halogen/hydrogen bonding patterns and other noncovalent interactions in the crystalline state. Concerning the syntheses, the efficient one-step synthesis of 9,9-diethylfluorene-2,4,7-tricarbaldehyde (8) is also worthy of particular mention.
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