The cathodic deprotection of the nitrobenzoyl group from phenyl nitrobenzoates in N,N-dimethylformamide

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Jorge, SMA
Stradiotto, N. R.

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Elsevier B.V.


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. (C) 1997 Elsevier B.V. S.A.



phenyl nitrobenzoates, cathodic deprotection, nitrobenzoyl group

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Journal of Electroanalytical Chemistry. Lausanne: Elsevier B.V. Sa Lausanne, v. 431, n. 2, p. 237-241, 1997.