Aromatic Nitration with Nitric Acid/Trifluoromethanesulfonic Anhydride

George A. Olah; V. Prakash Reddy; G. K. Surya Prakash

doi:10.1055/s-1992-26310

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

Abstract

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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.

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