Amines as Leaving Groups in Nucleophilic Aromatic Substitution Reactions. III. Hydrolysis of 1-Amino-2,4-dinitrobenzenes

ELBA I. BUJÁN; M. VIRGINIA REMEDI; RITA H. DE ROSSI

JOHN WILEY & SONS LTD

Lugar: LOndres; Año: 1995 vol. 8 p. 113 - 113

he kinetic study of the reaction of 1-pyrrolidino-2,4-dinitrobenzene, 1 -piperidino-2,4-dinitrobenzene and 1-morpholino-2,4-dinitrobenzene with NaOH in the presence and absence of the amine leaving group was carried out in aqueous solutions at 25"C, giving 2,4-dinitrophenol as the only product. A mechanism involving the formation of σ complexes by addition of HO- or the amine to the unsubstituted positions of the aromatic ring is proposed. These complexes were found to react faster than the original substrates.