Amines as Leaving Groups in Nucleophilic Aromatic Substitution Reactions.

ELBA I. BUJÁN; RITA H. DE ROSSI; ALICIA V. VEGLIA

AMER CHEMICAL SOC

Lugar: Washington; Año: 1986 vol. 51 p. 1976 - 1976

he hydrolysis reactions of N-(2,4dinitrophenyl)piperidine (7) and N-(2,4-dinitrophenyl)morpholine (8) were studied. Both reactions lead quantitatively to the formation of 2,4-dinitrophenol. They are second order toward the HO- concentration and are strongly catalyzed by the amine leaving group. The catalysis is interpreted in terms of the formation of 1,3-σ complexes with the amine or the HO-, which then react with another hydroxide ion to give the final product. The reactivity of the 1,3-σ complexes toward HO- is higher than that of the substrates themselves.