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Oxodiazonium ion generation 5. 3-(N-Nitroamino)-4-phenylfuroxan: synthesis and reactivity

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Abstract

3-(N-Nitroamino)-4-phenylfuroxan, the first representative of the furoxan series that contains the N-nitroamino group in position 3 of the furoxan ring, was obtained. This compound is not very stable; its structure was confirmed by chemical transformations into an ammonium salt and N- and O-methyl derivatives. Under standard conditions for oxodiazonium ion generation from nitramine, 3-(N-nitroamino)-4-phenylfuroxan underwent a transformation into the corresponding azofuroxan, viz., 3,3′-diazenediylbis(4-phenyl-1,2,5-oxadiazole 2-oxide), while the O-methyl derivative of 3-(N-nitroamino)-4-phenylfuroxan yielded 2-hydroxyimino-2-phenylacetonitrile. The changed reactivity of the oxodiazonium ion was explained by its intramolecular interaction with the exocyclic O atom of the furoxan system.

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Correspondence to A. M. Churakov.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 349–352, February, 2012.

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Zelenov, V.P., Voronin, A.A., Churakov, A.M. et al. Oxodiazonium ion generation 5. 3-(N-Nitroamino)-4-phenylfuroxan: synthesis and reactivity. Russ Chem Bull 61, 351–354 (2012). https://doi.org/10.1007/s11172-012-0048-z

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  • DOI: https://doi.org/10.1007/s11172-012-0048-z

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