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

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

Journal

Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285

Output data

Year: 2012, Volume: 61, Number: 2, Pages: 351-354 Pages count : 4 DOI: 10.1007/s11172-012-0048-z

Authors

Zelenov V.P. ¹ , Voronin A.A. ¹ , Churakov A.M. ¹ , Klenov M.S. ¹ , Strelenko Yu.A. ¹ , Tartakovsky V.A. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

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.

Zelenov V.P. , Voronin A.A. , Churakov A.M. , Klenov M.S. , Strelenko Y.A. , Tartakovsky V.A.
Oxodiazonium ion generation 5. 3-(N-Nitroamino)-4-phenylfuroxan: synthesis and reactivity
Russian Chemical Bulletin. 2012. V.61. N2. P.351-354. DOI: 10.1007/s11172-012-0048-z WOS Scopus OpenAlex

≡ Web of science:	WOS:000312068000017
≡ Scopus:	2-s2.0-84877040403
≡ OpenAlex:	W2008189274