Synthesis and properties of N-nitro-O-(4-nitrophenyl)hydroxylamine

Synthesis and properties of N-nitro-O-(4-nitrophenyl)hydroxylamine Full article

Journal

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

Output data

Year: 2009, Volume: 58, Number: 10, Pages: 2047-2057 Pages count : 11 DOI: 10.1007/s11172-009-0281-2

Authors

Klenov M.S. ¹ , Churakov A.M. ¹ , Anikin O.V. 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, Russia Federation

Salts of N-nitro-O-(4-nitrophenyl)hydroxylamine were synthesized by a new method of oxidative nitration, involving the reaction of O-(4-nitrophenyl)hydroxylamine with KNO2 or NaNO2 in the presence of PhI(OAc)2 or PhIO as oxidants. When using Na15NO2, the samples containing the nitro group labeled with the 15N isotope were obtained. Acidification of the appropriate salt gave N-nitro-O-(4-nitrophenyl)hydroxylamine. It is the first N-nitrohydroxylamine isolated in the H-form. Its thermal stability was investigated and the probable mechanism of decomposition was suggested. From a comparison of the 14N and 15N NMR spectra of N-nitro-O-(4-nitrophenyl)hydroxylamine with those of its O- and N-methylated derivatives, its equilibrium with the aci-form (N=NOOH) was inferred.

Klenov M.S. , Churakov A.M. , Anikin O.V. , Strelenko Y.A. , Tartakovsky V.A.
Synthesis and properties of N-nitro-O-(4-nitrophenyl)hydroxylamine
Russian Chemical Bulletin. 2009. V.58. N10. P.2047-2057. DOI: 10.1007/s11172-009-0281-2 WOS Scopus OpenAlex

≡ Web of science:	WOS:000280650300008
≡ Scopus:	2-s2.0-77955763978
≡ OpenAlex:	W2067737200