B3LYP/6-31G(d) calculations find that cubanes, persubstituted with NO2 or BF2 groups, are predicted to undergo near-barrierless, internal disrotations. However, as a consequence of the intrinsically higher energies of eclipsed conformations for threefold than for twofold rotors, the threshold mechanisms for octamethyl-, octakis(trifluoromethyl)-, octakis(trichloromethyl)-, octakis(tribromomethyl)-, octasilylcubane, and octakis(trichlorosilyl)cubane are calculated to be mono- or conrotation. The cubanes with the larger substituents are predicted to be O-symmetric, resolvable, and thus optically active.