Regioselective nitration of aromatic substrates in zeolite cages

Abstract

Phenol is nitrated regioselectively by fuming nitric acid inside the cages of faujasite zeolites (dependent on the loading level) and a remarkable ortho-selectivity is observed in solid state nitration. Toluene and chlorobenzene also containing ortho-/para-orienting substituents, undergo faster nitration, though the regioselectivity is less significant in zeolite media. The results are explained on the basis of diffusion and binding of phenol inside zeolite, which facilitate regioselectivity (and which is absent in toluene and chlorobenzene). Other advantages of employing zeolites as media for mild and selective nitration are also highlighted.