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

Zbigniew Wróbel; Andrzej Kwast

doi:10.1055/s-0030-1258230

PAPER

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;

Abstract

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Abstract

Anions generated from primary arylamines react with substituted nitrobenzenes to form σ^H-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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References

<A NAME="RZ17410SS-1A">1a</A> Terrier F. Nucleophilic Aromatic Displacement, The Influence of the Nitro Group Verlag Chemie; Weinheim: 1991.

<A NAME="RZ17410SS-1B">1b</A> Chupakhin ON. Charushin VN. van der Plas HC. Nucleophilic Aromatic Substitution of Hydrogen Academic Press; San Diego: 1994.

<A NAME="RZ17410SS-1C">1c</A> Mąkosza M. Russ. Chem. Bull. 1996, 45: 491

<A NAME="RZ17410SS-2A">2a</A> Mąkosza M. Staliński K. Pol. J. Chem. 1999, 73: 151

<A NAME="RZ17410SS-2B">2b</A> Mąkosza M. Staliński K. Tetrahedron 1998, 54: 8797

<A NAME="RZ17410SS-2C">2c</A> Mąkosza M. Staliński K. Chem. Eur. J. 2001, 7: 2025

<A NAME="RZ17410SS-2D">2d</A> Adam W. Mąkosza M. Zhao CG. Surowiec M.
J. Org. Chem. 2000, 65: 1099

<A NAME="RZ17410SS-3A">3a</A> Mąkosza M. Winiarski J. Acc. Chem. Res. 1987, 20: 282

<A NAME="RZ17410SS-3B">3b</A> Mąkosza M. Wojciechowski K. Liebigs Ann./Recl. 1997, 1805

<A NAME="RZ17410SS-3C">3c</A> Mąkosza M. Kwast A. J. Phys. Org. Chem. 1998, 11: 341

<A NAME="RZ17410SS-4A">4a</A> Wróbel Z. Tetrahedron Lett. 1997, 38: 4913

<A NAME="RZ17410SS-4B">4b</A> Wróbel Z. Tetrahedron 1998, 54: 2607

<A NAME="RZ17410SS-4C">4c</A> Wróbel Z. Eur. J. Org. Chem. 2000, 521

<A NAME="RZ17410SS-4D">4d</A> Wróbel Z. Pol. J. Chem. 1998, 72: 2384

<A NAME="RZ17410SS-4E">4e</A> Wróbel Z. Synlett 2004, 1929

<A NAME="RZ17410SS-5A">5a</A> Wohl A. Aue W. Ber. Dtsch. Chem. Ges. 1901, 34: 2442

<A NAME="RZ17410SS-5B">5b</A> Wohl A. Ber. Dtsch. Chem. Ges. 1903, 36: 4135

<A NAME="RZ17410SS-5C">5c</A> Serebryanyi SB. Uk. Khim. Zh. (Russ. Ed.) 1955, 21: 350

<A NAME="RZ17410SS-6A">6a</A> Stern MK. Hileman FD. Bashkin JK. J. Am. Chem. Soc. 1992, 114: 9237

<A NAME="RZ17410SS-6B">6b</A> Beska E, Toman P, Fiedler K, Hronec M, and Pinter J. inventors; US 6388136.

<A NAME="RZ17410SS-7A">7a</A> Fasani E. Pietra S. Albini A. Heterocycles 1992, 33: 573

<A NAME="RZ17410SS-7B">7b</A> Fasani E. Mella M. Albini A. J. Chem. Soc., Perkin Trans. 1 1992, 2689

<A NAME="RZ17410SS-7C">7c</A> Fischer O. Hepp E. Justus Liebigs Ann. Chem. 1889, 255: 145

<A NAME="RZ17410SS-7D">7d</A> Titova SP. Arinich AK. Gorelik MV. J. Org. Chem. USSR (Eng. Transl.) 1986, 1407

<A NAME="RZ17410SS-7E">7e</A> Okubo M. Inatomi Y. Taniguchi N. Imamura K. Bull. Chem. Soc. Jpn. 1988, 61: 3581

<A NAME="RZ17410SS-7F">7f</A> Jin D. Mandenhall D. Tetrahedron Lett. 1996, 37: 4881

<A NAME="RZ17410SS-8">8</A> Wróbel Z. Kwast A. Synlett 2007, 1525

<A NAME="RZ17410SS-9">9</A> Wirth S. Wallek AU. Zernickel A. Feil F. Sztiller-Sikorska M. Lesiak-Mieczkowska K. Bräuchle Ch. Lorenz I.-P. Czyż M. J. Inorg. Biochem. 2010, 104: 774

<A NAME="RZ17410SS-10">10</A> Mąkosza M. Lobanova O. Kwast A. Tetrahedron 2004, 60: 2577

<A NAME="RZ17410SS-11">11</A> Mąkosza M. Voskresensky S. Biaecki M. Kwast A. Pol. J. Chem. 1999, 73: 1969

<A NAME="RZ17410SS-12">12</A> Tsui K. Nakamura K. Konishi N. Okumura H. Matsuo M. Chem. Pharm. Bull. 1992, 40: 2399

<A NAME="RZ17410SS-13">13</A> Barluenga J. Fananas FJ. Sanz R. Fernandez Y. Chem. Eur. J. 1965, 397

Some signals very broad or invisible.

<A NAME="RZ17410SS-15">15</A> Kottenhahn AP. Seo ET. Stone HW. J. Org. Chem. 1963, 28: 3114

<A NAME="RZ17410SS-16">16</A> Cross B. Williams JP. Woodall RE. J. Chem. Soc. C 1971, 2085

<A NAME="RZ17410SS-17">17</A> Johnson HW. Iwata Y. J. Org. Chem. 1971, 36: 1921

<A NAME="RZ17410SS-18">18</A> Hunziker F. Kunzle F. Schmutz J. Helv. Chim. Acta 1966, 49: 244