The electrochemical cleavage of the nitrobenzoyl group from butyl nitrobenzoates in N,N-dimethylformamide
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Elsevier B.V.
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The applicability of the nitrobenzoyl group [NO2C6H4CO-] to protecting the functional hydroxyl group was investigated through study of the electrochemical behaviour of the butyl 4-, 3- and 2-nitrobenzoate compounds. These isomers are reduced in two cathodic steps. The first, at potentials of ca. -0.9 V vs. SCE, is attributed to the formation of rather stable anion radicals, involving one-electron transfer. The second, at potentials of ca. -1.7 V vs. SCE, occurs with a two-electron transfer in an ECE process, in which the dianion produced undergoes scission of the C-O bond giving n-butanoate ions with high yields (similar to 80%)
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Journal of Electroanalytical Chemistry. Lausanne 1: Elsevier B.V. Sa Lausanne, v. 415, n. 1-2, p. 27-32, 1996.
