Monoreduced 1,2-dihydrocorannuleneversusthe parent corannulene

Abstract

The monoanion of dihydrogenated corannulene isolated in the form of its potassium salt, namely tris(diglyme-κ3O,O′,O′′)potassium hexacyclo[11.5.2.04,17.07,16.010,15.014,18]icosa-1,3,5,7(16),8,10(15),11,13,17-nonaenide, [K(C6H14O3)3](C20H12), has been structurally characterized for the first time. The X-ray study confirms the previous NMR spectroscopic prediction that the two H atoms are attached to the same six-membered ring to form 1,2-dihydrocorannulene, thus destroying the aromaticity of only one arene ring of the corannulene core. The direct comparison of (C20H12)−with the parent corannulene anion, (C20H10)−, is provided to illustrate the geometry perturbations caused by rim hydrogenation.