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Synthesis 1992; 1992(11): 1087-1089
DOI: 10.1055/s-1992-26310
short paper
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Aromatic Nitration with Nitric Acid/Trifluoromethanesulfonic Anhydride

George A. Olah* , V. Prakash Reddy, G. K. Surya Prakash
  • *Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, Los Angeles, California 90089-1661, USA
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Publication Date:
17 September 2002 (online)

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Nitric acid/trifluoromethanesulfonic (triflic) anhydride was shown to be a highly effective electrophilic nitrating agent. A series of aromatics were nitrated under mild conditions in high yields. Similar results were also obtained when using nitric acid/trifluoromethane-sulfonic acid/phosphorus pentoxide as nitrating agent in nitroethane or nitromethane solution. The 15N NMR spectrum of 15N enriched nitric acid in triflic anhydride was studied and compared with that of other nitrating reagents. The data indicate the predominantly covalent nature of trifluoromethanesulfonyl nitrate formed in the systems.