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Issue 8, 2003
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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

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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.

Graphical abstract: 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

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Publication details

The article was received on 06 Feb 2003, accepted on 27 Feb 2003 and first published on 18 Mar 2003


Article type: Communication
DOI: 10.1039/B301491F
Citation: Chem. Commun., 2003,0, 1016-1017
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    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

    R. N. Butler, J. C. Stephens and L. A. Burke, Chem. Commun., 2003, 0, 1016
    DOI: 10.1039/B301491F

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