A slippery slope: mechanistic analysis of the intramolecular Scholl reaction of hexaphenylbenzene.
DFT calculations support an arenium cation-based mechanism for the Scholl reaction converting hexaphenylbenzene to hexa-peri-benzocoronene. The curve connecting fully benzenoid intermediates on the potential energy diagram is convex. This "slippery slope" provides an explanation for the ease of this cascade Scholl reaction. The calculated reaction coordinate predicts that intermediates will not accumulate; this prediction is verified by experiment.
Rempala
Pawel
P
Department of Chemistry, University of Nevada, Reno, Nevada 89557, USA.
Kroulík
Jirí
J
King
Benjamin T
BT