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Type: Artigo de periódico
Title: Regioselectivity of the nitration of phenol by acetyl nitrate adsorbed on silica gel
Author: Rodrigues, JAR
de Oliveira, AP
Moran, PJS
Custodio, R
Abstract: The reaction of phenol with acetyl nitrate in chloroform gives nitrophenol with an ortho/para ratio of 1.8. This ratio increase to 13.3 when the reaction was carried out with acetyl nitrate pre-adsorbed on dry silica gel. Silica may be acting as a template to bring phenol close to acetyl nitrate by hydrogen bonds forming a ternary complex, which undergoes a six-center rearrangement to o-nitrophenol. The formation of this ternary complex is evaluated by ab initio molecular orbital calculation, (C) 1999 Elsevier Science Ltd. All rights reserved.
Subject: nitration
nitric acid and derivatives
Country: Inglaterra
Editor: Pergamon-elsevier Science Ltd
Citation: Tetrahedron. Pergamon-elsevier Science Ltd, v. 55, n. 22, n. 6733, n. 6738, 1999.
Rights: fechado
Identifier DOI: 10.1016/S0040-4020(99)00320-8
Date Issue: 1999
Appears in Collections:Unicamp - Artigos e Outros Documentos

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