A fast and mild method for the nitration of aromatic rings

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Bak, Radoslaw and Smallridge, Andrew John (2001) A fast and mild method for the nitration of aromatic rings. Tetrahedron letters, 42 (38). pp. 6767-6769. ISSN 0040-4039


The use of N2O5 and a Fe(III) catalyst for the nitration of aromatic rings is described. This methodology is compatible with most functional groups and results in near quantitative yields in 4 min. The reaction conditions are non-oxidising: benzaldehyde and benzyl alcohols are readily nitrated with little or no oxidation (<4%) occurring. The addition of the iron catalyst activates the system to such an extent that nitration of an activated aromatic ring, such as toluene, occurs quantitatively at −100°C. This high activity allows compounds with sensitive functional groups such as alkenes to be smoothly nitrated.

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Item type Article
URI https://vuir.vu.edu.au/id/eprint/1098
DOI 10.1016/S0040-4039(01)01378-8
Official URL http://dx.doi.org/10.1016/S0040-4039(01)01378-8
Subjects Historical > RFCD Classification > 290000 Engineering and Technology
Historical > Faculty/School/Research Centre/Department > School of Engineering and Science
Keywords aromatic rings, methodology, N2O5, Fe(III)
Citations in Scopus 79 - View on Scopus
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