Journal of Organic Chemistry p. 1976 - 1981 (1986)
Update date:2022-08-29
Topics:
Vargas, Elba B. de
Rossi, Rita H. de
Veglia, Alicia V.
The hydrolysis reactions of N-(2,4-dinitrophenyl)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-? 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-? complexes toward HO- is higher than that of the substrates themselves.
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