[C:1]1([N:7]2[C:11](=[O:12])[N:10]=[N:9][NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.F[B-](F)(F)F.[O:18]=[N+:19]=[O:20].O>C(#N)C>[N+:19]([C:4]1[CH:3]=[CH:2][C:1]([N:7]2[C:11](=[O:12])[N:10]=[N:9][NH:8]2)=[CH:6][CH:5]=1)([O-:20])=[O:18]A solution of 1-phenyl-5-tetrazolone (30 g) in acetonitrile (300 mL) was stirred under argon at 0° C. and nitronium tetrafluoroborate (36.9 g) was added over 30 minutes. After stirring at 0° C. for an additional 30 minutes the mixture was poured into water (900 mL). The precipitate was collected by filtration and dried under vacuum to give 23.1 g of the title compound as cream-colored solids. The filtrate was extracted with ethyl acetate, dried (MgSO4), filtered, and concentrated to give an additional 8.6 g of solids which was a 1:1 mixture of ortho- and para-substituted isomers. 1H NMR (acetone-d6) δ 13.62 (br s, 1 H), 8.36 (ABq, JAB =9.2 Hz, 4 H); MS (EI) m/z 207 (M+); Rf=0.2 (10% methanol/dichloromethane).
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