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

Literature Information

Publication Date 2003-03-18
DOI 10.1039/B301491F
Impact Factor 6.222
Authors

R. N. Butler, John C. Stephens, Luke A. Burke


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Abstract

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 °C produced p-benzoquinone. 15N NMR spectra suggest that pentazole, HN5, was also produced and held in solution as N5− with Zn2+ ion. The 15N signal from N5− was −10.0 ± 2.0 ppm in agreement with calculated values.

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