Improved nitrations using metal nitrate-sulfuric acid systems
Improved nitrations using metal nitrate-sulfuric acid systems
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.
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
8019-8024
Mellor, J. M.
d9b993ad-31be-4f91-8ea3-1723cd1c23bc
Mittoo, S.
595c0eca-0eea-4e8c-aaf8-936a1a438d48
Parkes, R.
de291367-db7c-4da3-8bfe-7d9f7b93bc9c
Millar, R. W.
70ba057b-dd41-43e4-b514-2c0751af9252
29 September 2000
Mellor, J. M.
d9b993ad-31be-4f91-8ea3-1723cd1c23bc
Mittoo, S.
595c0eca-0eea-4e8c-aaf8-936a1a438d48
Parkes, R.
de291367-db7c-4da3-8bfe-7d9f7b93bc9c
Millar, R. W.
70ba057b-dd41-43e4-b514-2c0751af9252
Mellor, J. M., Mittoo, S., Parkes, R. and Millar, R. W.
(2000)
Improved nitrations using metal nitrate-sulfuric acid systems.
Tetrahedron, 56 (40), .
(doi:10.1016/S0040-4020(00)00720-1).
Abstract
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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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
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Date deposited: 16 Dec 2005
Last modified: 15 Mar 2024 06:10
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Contributors
Author:
J. M. Mellor
Author:
S. Mittoo
Author:
R. Parkes
Author:
R. W. Millar
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