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

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dc.contributor.authorJorge, SMA
dc.contributor.authorStradiotto, N. R.
dc.contributor.institutionUniversidade de São Paulo (USP)
dc.contributor.institutionUniversidade Estadual Paulista (Unesp)
dc.date.accessioned2014-05-20T15:25:11Z
dc.date.available2014-05-20T15:25:11Z
dc.date.issued1997-07-15
dc.description.abstractThe 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.en
dc.description.affiliationUSP,FAC FILOSOFIA CIENCIAS & LETRAS RIBEIRAO PRET,DEPT QUIM,BR-14040901 RIBEIRAO PRET,SP,BRAZIL
dc.format.extent237-241
dc.identifierhttp://dx.doi.org/10.1016/S0022-0728(97)00257-X
dc.identifier.citationJournal of Electroanalytical Chemistry. Lausanne: Elsevier B.V. Sa Lausanne, v. 431, n. 2, p. 237-241, 1997.
dc.identifier.doi10.1016/S0022-0728(97)00257-X
dc.identifier.issn0022-0728
dc.identifier.urihttp://hdl.handle.net/11449/35644
dc.identifier.wosWOS:A1997YD51200012
dc.language.isoeng
dc.publisherElsevier B.V.
dc.relation.ispartofJournal of Electroanalytical Chemistry
dc.rights.accessRightsAcesso restrito
dc.sourceWeb of Science
dc.subjectphenyl nitrobenzoatespt
dc.subjectcathodic deprotectionpt
dc.subjectnitrobenzoyl grouppt
dc.titleThe cathodic deprotection of the nitrobenzoyl group from phenyl nitrobenzoates in N,N-dimethylformamideen
dc.typeArtigo
dcterms.licensehttp://www.elsevier.com/about/open-access/open-access-policies/article-posting-policy
dcterms.rightsHolderElsevier B.V.
unesp.author.orcid0000-0002-8779-9585[2]
unesp.author.orcid0000-0002-1227-5242[2]

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