Theory predicts that the benzotricyclobutene molecule would be conformationally non-planar. Localization of the double bonds exocyclic to the three fused-cyclobutane groups are expected in the "aromatic" nucleus. As a consequence, the molecule will be expected to behave like a triene rather than a benzenoid aromatic compound. It was hoped that a one-step synthesis of the benzotricyclobutene molecule could be achieved by the displacement of the bromine atoms in the hexakis(α-bromomethyl)benzene molecule by "active" metallic cations. The displacement however was not at all a facile one. In protonic solvents hexamethylbenzene was obtained from hexakis(α-bromomethyl)benzene; in non-protonic solvents, no reaction occurred. The most promising route of this molecule would be by the pyrolysis of the 1,3,4,6,7,9-hexahydrobenzo(1,2-c:3,4-c':5,6-c")trithiophene-2,2,5,5,8,8-hexoxide (CXVI) via the intermediary sulfide (CXIV), based on the work of Cava and co-workers. Although the synthesis of benzo(1,2:3,4:5,6)tricyclobutene was not achieved, there is good evidence that the intermediate 1,3,4,6,7,9-hexahydrobenzo(1,2-c:3,4-c':5,6-c")trithiophene was synthesized.
