Addition of dihalocarbenes to corannulene. A fullerene-type reaction

Dihalocarbenes (:CCl2, :CBr2, and :CI2) add preferentially to one of the radial double bonds of corannulene, rather than to the rim. These cyclopropanations strongly resemble the additions of dihalocarbenes to fullerenes, which likewise occur at 6:6-double bonds, destroy the cyclic conjugation in two adjacent benzene rings, and give ‘closed’ adducts. An explanation is offered for the abnormally high reactivity of the interior carbon atoms of corannulene.