Hydrolysis of ethers of 2,4-dinitrophenol. No evidence for a single electron transfer mechanism

Article abstract of DOI:10.1021/jo00078a012

The 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 S(N)Ar 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.