Improved nitrations using metal nitrate-sulfuric acid systems

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).


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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.

Item Type: Article
Digital Object Identifier (DOI): doi:10.1016/S0040-4020(00)00720-1
ISSNs: 0040-4020 (print)
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
ePrint ID: 19004
Date :
Date Event
29 September 2000Published
Date Deposited: 16 Dec 2005
Last Modified: 16 Apr 2017 23:07
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