Tetrahedron p. 6733 - 6738 (1999)
Update date:2022-08-11
Topics:
Augusto
Rodrigues
De Oliveira Filho, Antonio Pedro
Moran, Paulo J. S.
Custodio, Rogerio
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.
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