Practical and Efficient Synthesis of 4,4′-Dihydroxy-3,3′-dinitrodiphenyl Ether and 1,3-bis(4-Hydroxy-3-nitrophenoxy)benzene in Aqueous Alkaline Medium

A Probable Hydrogen-Bonded Meisenheimer Complex: An Unusually High SNAr Reactivity of Nitroaniline Derivatives with Hydroxide Ion in Aqueous Media

“…Typically, readily available 4-nitrochlorobenzene and its derivatives (L = Cl, 1 , Scheme ) that contain Cl with a moderately high leaving ability are used as substrates for S N Ar reactions . On the other hand, as depicted even in textbooks, derivatives of 4-nitroaniline (L = NH 2 , 2 ) only reluctantly undergo S N Ar reactions in which the poor leaving group (NH 2 ) is eliminated. − …”