Nitrosoarenes react with nitrogen monoxide (nitric oxide) at room temperature and in aprotic media to afford the corresponding diarylnitroxides by the intermediate formation of N-nitrosoarylnitroxides. However, these latter spin adducts, in contrast with literature reports, have never been detected by us. N-nitrosophenylnitroxide is obtained only in the oxidation of the ammonium salt of N-nitrosophenylhydroxylamine (cupferron) with trace amounts of lead tetraacetate. However, it evolves with time to diphenylnitroxide, as demonstrated by following the reaction course in the ESR cavity, On a macroscale level, the reaction between nitrosobenzene and nitric oxide leads to the formation of N-nitrosodiphenylamine, 4-nitro-N-nitrosodiphenylamine, 4-nitrodiphenylamine and 4,4'-dinitrodiphenylamine, in addition to diphenylnitroxide. Diarylnitroxides are also obtained when nitrosoarenes react with small amounts of nitrogen dioxide; the mechanism of this reaction is proposed and discussed. The structure of 4-nitro-N-nitrosodiphenylamine was determined by X-ray analysis.

Reactions of Nitrosoarenes with Nitrogen Monoxide (Nitric Oxide) and Nitrogen Dioxide: Formation of Diarylnitroxides / Astolfi, Paola; Carloni, Patricia; Damiani, Elisabetta; Greci, Lucedio; M., Marini; C., Rizzoli; Stipa, Pierluigi. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 19:(2008), pp. 3279-3285. [10.1002/ejoc.200800213]

Reactions of Nitrosoarenes with Nitrogen Monoxide (Nitric Oxide) and Nitrogen Dioxide: Formation of Diarylnitroxides.

ASTOLFI, PAOLA;CARLONI, PATRICIA;DAMIANI, Elisabetta;GRECI, Lucedio
;
STIPA, Pierluigi
2008-01-01

Abstract

Nitrosoarenes react with nitrogen monoxide (nitric oxide) at room temperature and in aprotic media to afford the corresponding diarylnitroxides by the intermediate formation of N-nitrosoarylnitroxides. However, these latter spin adducts, in contrast with literature reports, have never been detected by us. N-nitrosophenylnitroxide is obtained only in the oxidation of the ammonium salt of N-nitrosophenylhydroxylamine (cupferron) with trace amounts of lead tetraacetate. However, it evolves with time to diphenylnitroxide, as demonstrated by following the reaction course in the ESR cavity, On a macroscale level, the reaction between nitrosobenzene and nitric oxide leads to the formation of N-nitrosodiphenylamine, 4-nitro-N-nitrosodiphenylamine, 4-nitrodiphenylamine and 4,4'-dinitrodiphenylamine, in addition to diphenylnitroxide. Diarylnitroxides are also obtained when nitrosoarenes react with small amounts of nitrogen dioxide; the mechanism of this reaction is proposed and discussed. The structure of 4-nitro-N-nitrosodiphenylamine was determined by X-ray analysis.
2008
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11566/51506
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