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Synthesis 2010(22): 3865-3872  
DOI: 10.1055/s-0030-1258230
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Simple Synthesis of N-Aryl-2-nitrosoanilines in the Reaction of Nitroarenes with Aniline Anion Derivatives

Zbigniew Wróbel*, Andrzej Kwast
Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44/52, 01-224 Warsaw, Poland
Fax: +48(22)6318788; e-Mail: wrobel@icho.edu.pl;
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Publication History

Received 7 July 2010
Publication Date:
25 August 2010 (online)

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Abstract

Anions generated from primary arylamines react with substituted nitrobenzenes to form σH-adducts, which, under basic reaction conditions, undergo transformation to N-aryl-2-nitroso­amines. Competitive substitution of reactive halogens in the nitro­arenes, which is observed in certain cases, can be controlled by the solvent selected.

Key words

nucleophilic additions - arenes - amines - nitroso group

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