Organic photochemistry. Part IV. Photonucleophilic substitution reactions of monosubstituted benzenes

Abstract

Excitation of the 280 mµ absorption band of monosubstituted benzenes such as fluorobenzene, chlorobenzene, and anisole in the presence of good nucleophiles, leads to a displacement of the substituent by the nucleophile. The reaction appears to involve neither radical nor benzyne intermediates, and is interpreted as an ionic mechanism proceeding by attack of the nucleophile at the electron-deficient centres of the excited state of the aromatic component.