S. M. A. Jorge, N. Stradiotto
Jul 15, 1997
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Influential Citations
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Journal
Journal of Electroanalytical Chemistry
Abstract
The reduction of phenyl benzoates with nitro substituents at the 2-, 3- and 4-positions of the benzoates in N, N-dimethylformamide is reported. The phenyl 4- and 3-nitrobenzoate are reduced in two cathodic steps. The first one, at about −0.9 V vs. SCE, a reversible one-electron process, gives a rather stable anion radical. The second reduction step at potentials between −1.5 and −2.0 V vs. SCE leads to formation of the dianion, which decomposes giving free phenol in good yields ( > 80%). On the other hand, the phenyl 2-nitrobenzoate is reduced in one cathodic step. This step occurs at −0.9 V with formation of an unstable anion radical which decomposes via C-O bond cleavage, giving phenol with a yield of ca. 80%. The mechanisms of the reduction of these compounds are discussed.