The simplest homoaromatic analogue of benzene with a potential through-space homoconjugation, cycloheptatriene 1, has been discussed as prototypical homoaromatic (Fig. , top) . Calculations indicate a homoaromatic character; however, no experimental data exist to support this claim . For the prototypical through-bond homoaromatic norcaradiene 2, calculations show no indication for homoaromaticity .