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Type: Artigo de periódico
Title: Suicide Nucleophilic Attack: Reactions of Benzohydroxamate Anion with Bis(2,4-dinitrophenyl) Phosphate
Author: Orth, ES
da Silva, PLF
Mello, RS
Bunton, CA
Milagre, HMS
Eberlin, MN
Fiedler, HD
Nome, F
Abstract: The reaction between the benzohydroxamate anion (BHO(-)) and bis(2,4-dinitrophenyl) phosphate (BDNPP) has been examined kinetically, and the products were characterized by mass and NMR spectroscopy. The nucleophilic attack of BHO- follows two reaction paths: (i) at phosphor-us, giving an unstable intermediate that undergoes a Lossen rearrangement to phenyl isocyanate, aniline, diphenylurea, and O-phenylcarbamyl benzohydroxamate: and (ii) on the aromatic carbon, giving an intermediate that was detected but slowly decomposes to aniline and 2,4-dinitrophenol. Thus, the benzohydroxamate anion can be considered a self-destructive molecular scissor since it reacts and loses its nucleophilic ability.
Country: EUA
Editor: Amer Chemical Soc
Citation: Journal Of Organic Chemistry. Amer Chemical Soc, v. 74, n. 14, n. 5011, n. 5016, 2009.
Rights: fechado
Identifier DOI: 10.1021/jo9007354
Date Issue: 2009
Appears in Collections:Unicamp - Artigos e Outros Documentos

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