Tetrahedron

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

JAR Rodrigues, AP de Oliveira Filho, PJS Moran…

文献索引：Augusto; Rodrigues; De Oliveira Filho, Antonio Pedro; Moran, Paulo J. S.; Custodio, Rogerio Tetrahedron, 1999 , vol. 55, # 22 p. 6733 - 6738

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被引用次数: 56

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 ...