Octaphenylnaphthalene and Decaphenylanthracene

Abstract

Octaphenylnaphthalene (2) was synthesized by the addition of tetraphenylbenzyne to tetraphenylcyclopentadienone, and decaphenylanthracene (3) was synthesized by the addition of the same aryne to hexaphenylisobenzofuran followed by deoxygenation of the adduct. The structures of both compounds were determined by X-ray analysis. Compound 2 adopts a conformation of approximate Ci symmetry with a slightly undulating naphthalene nucleus, but compound 3 exhibits C2 (and approximate D2) symmetry with a 63° twist of the central anthracene.