Regioselectivity of the nitration of phenol by acetyl nitrate adsorbed on silica gel

被引：61

作者：

Rodrigues, JAR ^{[1
]}

de Oliveira, AP ^{[1
]}

Moran, PJS ^{[1
]}

Custódio, R ^{[1
]}

机构：

[1] Univ Estadual Campinas, Inst Quim, BR-13083970 Campinas, SP, Brazil

来源：

TETRAHEDRON | 1999年 / 55卷 / 22期

关键词：

nitration; nitric acid and derivatives; phenols; regioselection;

D O I：

10.1016/S0040-4020(99)00320-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：6733 / 6738

页数：6

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