Diindeno[1,2,3,4-defg;1′,2′,3′,4′-mnop]chrysenes: solution-phase synthesis and the bowl-to-bowl inversion barrier

Abstract

Diindeno[1,2,3,4-defg;1′,2′,3′,4′-mnop]chrysenes 2 were straightforwardly prepared in around 20% yield from 9,10-diarylphenanthrenes 3 by palladium-catalyzed intramolecular arylations. The bowl-to-bowl inversion barrier for buckybowl 2-iPr is predicted to be approximately 7 kcal mol⁻¹ based on density functional theory calculations and this value is consistent with the results of a variable-temperature ¹H-NMR study.