The synthesis of dicyclopententobenzocyclobutene from 1, 1-dicyclopentenyl and dimethyl cyclobutene-1, 2-dicarboxylate is described. Current theories regarding sterically induced aromatic bond alternation would predict that both the σ and π frameworks should show more double bond character exocyclic to the small fused rings. The structural parameters of dicyclopentenobenzocyclobutene have been determined by single crystal X-ray analysis. ...