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The synthesis of the bi[10]paracyclophanes 2 and 4 from the meso-configured bioxepine 3 is described. These compounds are stereochemically remarkable: the biaryl axis that connects the constitutionally identical, but oppositely configured planar-chiral paracyclophane portions, is configurationally semi-stable. Thus, 2 is an unprecedented borderline case of a (planar-chiral)–(axially chiral)–(planar-chiral)...
A preparative synthesis of novel bioxepines and bi[10]paracyclophanes with meso- and rac-configuration is described. The bi[10]paracyclophane (-)-6b with two elements of planar chirality and one chiral axis has been obtained in enantiomerically pure form. Its absolute configuration was determined by quantum chemical calculation of the circular dichroism and comparison with the experimental CD spectrum.
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