Aromatic Nitration with Nitric Acid/trifluoromethanesulfonic Anhydride
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/trifluoromethanesulfonic 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.
G. A. Olah et al., "Aromatic Nitration with Nitric Acid/trifluoromethanesulfonic Anhydride," Synthesis, Georg Thieme Verlag, Nov 1992.
The definitive version is available at http://dx.doi.org/10.1055/s-1992-26310
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© 1992 Georg Thieme Verlag, All rights reserved.