Strain-Relief-Driven Rearrangement of [2.2]Paracyclophane Derivatives in the Synthesis of Biarylophanes

The prospect of applying the Scholl reaction to [2.2]paracyclophanes without oxidative bridge cleavage was investigated using a set of three aryl-substituted derivatives. In each case, rupture of the [2.2]paracyclophane framework could not be circumvented but led instead to a set of structurally unusual fluorescent biarylophanes (ΦF up to 0.60) with differing regioselectivity in the final ring closure.