The cathodic deprotection of the nitrobenzoyl group from phenyl nitrobenzoates in N,N-dimethylformamide
dc.contributor.author | Jorge, SMA | |
dc.contributor.author | Stradiotto, N. R. | |
dc.contributor.institution | Universidade de São Paulo (USP) | |
dc.contributor.institution | Universidade Estadual Paulista (Unesp) | |
dc.date.accessioned | 2014-05-20T15:25:11Z | |
dc.date.available | 2014-05-20T15:25:11Z | |
dc.date.issued | 1997-07-15 | |
dc.description.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. (C) 1997 Elsevier B.V. S.A. | en |
dc.description.affiliation | USP,FAC FILOSOFIA CIENCIAS & LETRAS RIBEIRAO PRET,DEPT QUIM,BR-14040901 RIBEIRAO PRET,SP,BRAZIL | |
dc.format.extent | 237-241 | |
dc.identifier | http://dx.doi.org/10.1016/S0022-0728(97)00257-X | |
dc.identifier.citation | Journal of Electroanalytical Chemistry. Lausanne: Elsevier B.V. Sa Lausanne, v. 431, n. 2, p. 237-241, 1997. | |
dc.identifier.doi | 10.1016/S0022-0728(97)00257-X | |
dc.identifier.issn | 0022-0728 | |
dc.identifier.uri | http://hdl.handle.net/11449/35644 | |
dc.identifier.wos | WOS:A1997YD51200012 | |
dc.language.iso | eng | |
dc.publisher | Elsevier B.V. | |
dc.relation.ispartof | Journal of Electroanalytical Chemistry | |
dc.rights.accessRights | Acesso restrito | |
dc.source | Web of Science | |
dc.subject | phenyl nitrobenzoates | pt |
dc.subject | cathodic deprotection | pt |
dc.subject | nitrobenzoyl group | pt |
dc.title | The cathodic deprotection of the nitrobenzoyl group from phenyl nitrobenzoates in N,N-dimethylformamide | en |
dc.type | Artigo | |
dcterms.license | http://www.elsevier.com/about/open-access/open-access-policies/article-posting-policy | |
dcterms.rightsHolder | Elsevier B.V. | |
unesp.author.orcid | 0000-0002-8779-9585[2] | |
unesp.author.orcid | 0000-0002-1227-5242[2] |
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