Abstract
Cyclo[8]isoindole 3 is prepared by retro-Diels-Alder reaction of 2 under thermal conditions. The optimized synthesis of compound 2 is based on oxidative homocoupling of 1 in the presence of Ce(IV) as oxidant and SO4 ²- as template. Optical properties of compound 2 and 3 are explored and rationalized based on magnetic circular dichroism spectroscopy and DFT calculations. X-ray crystallography revealed that cyclo[8]pyrrole 2 possesses a near-planar geometry, whereas compound 3 is strongly distorted owing to steric hindrance between the neighboring benzene rings.
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