Effect of fluoro substitution on the packing motifs of benzylidene- and dibenzylidene-cyclopentanones
Date
1991ISSN
1472-779XSource
Journal of the Chemical Society, Perkin Transactions 2Issue
8Pages
1131-1135Google Scholar check
Metadata
Show full item recordAbstract
The structure and solid-state reactivity of one fluorinated benzyl(benzylidene)cyclopentanone and two fluorinated dibenzylidenecyclopentanones are reported and the influence of fluoro substitution upon the packing of benzylidenecyclopentanones is discussed. It was shown that intermolecular atom-atom interactions involving the fluoro groups hold sway over the effect of the volume of the substituents upon crystal packing. As a result, the two dibenzylidene compounds have packing motifs very different from that of the unsubstituted parent compound, and thus a different solid-state reactivity pattern. Both the fluorinated dibenzylidene compounds undergo topochemical solid-state dimerisation, whereas the fluorobenzylidene compound was found to be photostable.