Tetrahedron

… : Part 10. The nitration of phenols by pyridine derivatives carrying a transferable nitro group11Part 9. SO Onyiriuka and CJ Suckling, J. Org. Chem., 1986, 51, 1900.

…, SO Onyiriuka, L Rees, JR Rooney, CJ Suckling

Index: Pervez,Humayun; Onyiriuka, Samuel O.; Rees, Lilias; Rooney, James R.; Suckling, Colin J. Tetrahedron, 1988 , vol. 44, # 14 p. 4555 - 4568

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Citation Number: 34

Abstract

Pyridinium salts bearing carboxylate side chains and pyridones are shown to react with nitronium tetrafluoroborate or nitrogen dioxide to yield activated intermediates capable of selectively nitrating phenol ortho to the hydroxyl group with virtually complete selectivity and in quantitative yield in aprotic solvents. Although the nitration of phenol itself is exceptionally selective, the nitration of some substituted phenols lead to mixtures of mononitrated ...