Chiral Atropisomeric Indenocorannulene Bowls: Critique of the Cahn-Ingold-Prelog Conception of Molecular Chirality

Abstract

Chiral corannulenes abound, but suffer generally from configurational lability associated with bowl-to-bowl inversion,[1] thus obviating questions of stereogenicity and stereoelement construction.[2] In contrast, peri-annulated corannulenes show greatly increased barriers for bowl-to-bowl inversion; specifically indenocorannulenes invert on a time scale too slow to observe by normal NMR methods and raise the possibility of creating chiral atropisomeric bowl-shaped aromatics.[3] Two methods for preparing indenocorannulene from simple 2 Show more