Synthesis and Adiabatic Photochemistry of a 1,4-Difluorobenzene – Naphthalene Biplanemer

Abstract

A naphtalene-1,4-difluorobenzene biplanemer 1a has been prepared through the electrolytic oxidative didecarboxylation. The direct irradiation of 1a gave 1,4-difluorobenzene and excited naphthalene in both a singlet state (Φ_f = 0.098) and a triplet state (Φ_p = 0.029) at 77 K in EPA. In the triplet-sensitized reaction, the biplanemer 1a underwent intramolecular [2π+2π] cycloaddition to give a cage compound instead of the formation of the triplet naphthalene.