Hydrolysis of Ethers of 2,4-dinitrophenol. No Evidence for a Single Electron Transfer Mechanism.

ELBA I. BUJÁN; EDUARDO L. SETTI; MARIO L. AIMAR; RITA H. DE ROSSI

AMER CHEMICAL SOC

Lugar: Washington; Año: 1993 vol. 58 p. 7364 - 7364

he reactions of 3-butenyl-2,4-dinitrophenyl ether (1), allyl 2,4-dinitrophenyl ether (5), and n-butyl 2,4-dinitrophenyl ether (6) with KOH in two DMSO-water mixtures (50% v/v and 70% v/v) were studied. In all cases, no evidence was found for a single electron transfer mechanism; 2,4-dinitrophenol was the only product formed. The reaction follows the classical SNAr mechanism. The order of reactivity is 5 > 1 > 6 in both solvents, although the reactivities differ only by factors of 1.4 and 2 in 50 and 70% DMSO, respectively.