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Improved nitrations using metal nitrate-sulfuric acid systems

Record type: Article

Procedures for efficient mono- and di-nitration of aromatic substrates have been developed using eerie ammonium nitrate suspended in dichloromethane in the presence of 2 equiv. of sulfuric acid. By suspending the sulfuric acid on silica gel following nitration, products are easily isolated by filtration and evaporation of solvent. In these nitrations eerie ammonium nitrate can be replaced by other metal nitrates, for example potassium- or tetrabutylammonium-nitrate. In contrast the nitration of naphthalene by eerie ammonium nitrate in the presence of methanol and sulfuric acid affords a mixture of 1,4- and 1,2-methoxynitronaphthalenes, but these nitrations cannot be achieved using potassium or tetrabutylammonium nitrate. The mechanism of this nitration/oxidation is discussed.

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Citation

Mellor, J. M., Mittoo, S., Parkes, R. and Millar, R. W. (2000) Improved nitrations using metal nitrate-sulfuric acid systems Tetrahedron, 56, (40), pp. 8019-8024. (doi:10.1016/S0040-4020(00)00720-1).

More information

Published date: 29 September 2000
Keywords: cerie ammonium nitrate, naphthalene, nitration, silica gel cerium(iv) ammonium-nitrate, ozone-mediated nitration, aromatic-compounds, silica-gel, recyclable catalysts, nitrogen-dioxide, nitric-acid, regioselectivity, lanthanide(iii), mononitration

Identifiers

Local EPrints ID: 19004
URI: http://eprints.soton.ac.uk/id/eprint/19004
ISSN: 0040-4020
PURE UUID: e8bcc472-acbb-4e0f-ae76-409c2659ddc9

Catalogue record

Date deposited: 16 Dec 2005
Last modified: 17 Jul 2017 16:34

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Contributors

Author: J. M. Mellor
Author: S. Mittoo
Author: R. Parkes
Author: R. W. Millar

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