The significance of Kekulé structures for the stability of aromatic systems—II

Dihydroheptazethrene (V) and 1:14,11:12-dibenzo-5,7-dihydro-pentacene (VI) were synthesized. The former gave heptazethrene (VII) on dehydrogenation, whilst the latter polymerized immediately. This difference is explained by the fact that heptazethrene (VII) can be formulated with a Kekulé structure and the dehydrogenation product of VI cannot. Heptazethrene is a basis hydrocarbon and is closely related to dibenzoheptazethrene (VIII). Heptazethrenequinone (II) is a true quinone giving a blue vat, whilst the isomer (IV) is a diketone and does not give a vat.