The regioselectivity of the intramolecular Scholl reaction has been investigated with the study of test molecules bearing bulky tert-butyl substituents and offering competing cyclization pathways to non-congested products and highly congested alternatives. Surprisingly, even a strong steric hindrance has no marked effect on regioselectivity and highly twisted polycyclic aromatic hydrocarbons are preferentially formed. These results, including a synthesis of triply helical hexa-tert-butyl-hexabenzotriphenylene, suggest that this reaction may be considered for the synthesis of highly strained polycyclic aromatic hydrocarbons.

Strongly twisted arenes by Scholl cyclizations with unexpected regioselectivity

243rd National Meeting (2012)

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