Abstract
Preparation of the regiospecifically trifluoromethyl substituted dibenzosemibullvalenes3 and5 is described. An unequivocal proof of chirality of3 and5 was obtained by enrichment of their enantiomers using liquid chromatography on triacetyl- or tribenzoylcellulose. The stereostructure of compounds3 to5 was proved by their1H-NMR spectra and confirmed by X-ray crystallographic analysis. The geometrical data from X-ray structural analyses showed that five-membered rings involved in the skeleton of3 and5 adopt flattened envelope conformations. These results indicate also a significant substituent-induced bond length asymmetry in the cyclopropane rings of3 and5.
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