First generation of pentazole (HN5, pentazolic acid), the final azole, and a zinc pentazolate salt in solution:: A new N-dearylation of 1-(p-methoxyphenyl) pyrazoles, a 2-(p-methoxyphenyl) tetrazole and application of the methodology to 1-(p-methoxyphenyl) pentazole

Ceric ammonium nitrate (CAN) in methanol-water gave a new N-dearylation of a series of substituted 1-(p-methoxyphenyl) pyrazoles and a 2-(p-methoxyphenyl)tetrazole producing p-benzoquinone and the parent azole in a mole for mole ratio. Application of this reaction to 1-(p-methoxyphenyl) pentazole at -40 degreesC produced p-benzoquinone. N-15 NMR spectra suggest that pentazole, HN5, was also produced and held in solution as N-5(-) with Zn2+ ion. The N-15 signal from N-5(-) was -10.0 +/- 2.0 ppm in agreement with calculated values.