Abstract

(±)-[3 2](1,4)Barrelenophane was completely resolved into its enantiomers by HPLC separation using a chiral stationary phase (Chiralcel OD) with hexane/propan-2-ol (1:9). The specific rotations and circular dichroism spectra of (+)- and (−)-[3 2](1,4)barrelenophanes indicated the enantiomeric relationships. The longest absorption band at 360 nm ( ε 541, CH 2Cl 2) is identified mainly as AN intramolecular charge transfer band between the benzene ring and the double bond conjugated with cyano groups. The X-ray structure of the (+)-isomer has been determined.

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