Base-mediated Reaction of Quaternary Ammonium Salts with Nitroarenes - Their Useful Functionalization via Vicarious Nucleophilic Substitution (VNS)

Andrzej Jończyk; Anna Kowalkowska

doi:10.1055/s-2002-23546

PAPER

Base-mediated Reaction of Quaternary Ammonium Salts with Nitroarenes - Their Useful Functionalization via Vicarious Nucleophilic Substitution (VNS)

Andrzej Jończyk*, Anna Kowalkowska
Warsaw University of Technology, Faculty of Chemistry, Koszykowa 75, 00-662 Warszawa, Poland
Fax: +48(22)6282741; e-Mail: anjon@ch.pw.edu.pl;

Abstract

All articles of this category

Abstract

Ammonium ylides generated from ammonium salt 1a-e with a base react with derivatives of 3-nitropyridine 2a-c and 2-nitrothiophene (3) to form products of vicarious nucleophilic substitution (VNS) 7, 8, or 9 respectively. The products of VNS 10, 11, or 12 are also produced from the corresponding ammonium salts, a base and 4-chloro-nitrobenzene (4), nitrobenzene (5), or 1-nitronaphthalene (6), respectively. In a few products, an exchange of alkoxy group 7c or substitution of chlorine by alkoxyl 8a,b occured.

Key words

ylides - nucleophilic aromatic substitution - nitriles - esters - amides

Full Text

References

1 Mąkosza M. Winiarski J. Acc. Chem. Res. 1987, 20: 282

2 Mąkosza M. Danikiewicz W. Wojciechowski K. Phosphorus, Sulfur, Silicon Relat. Elem. 1999, 53: 457

3 Mąkosza M. Synthesis 1991, 103

4 Mąkosza M. Mudryk B. Tetrahedron 1988, 44: 209

5 Traynelis VJ. McSweeney JV. J. Org. Chem. 1966, 31: 243

6 Tanaka A. Usui T. J. Heterocycl. Chem. 1979, 16: 1409

7 Jończyk A. Konarska A. Synlett 1999, 1085

8 Mąkosza M. Chylińska B. Mudryk B. Liebigs Ann. Chem. 1984, 8

9 Mąkosza M. Danikiewicz W. Wojciechowski K. Liebigs Ann. Chem. 1988, 203

10 Mąkosza M. Winiarski J. J. Org. Chem. 1984, 49: 1494

11 Mąkosza M. Sypniewski M. Glinka T. Tetrahedron 1996, 52: 3189

12 Strazzolini P. Giumanini AG. Runcio A. Scuaccato M. J. Org. Chem. 1998, 63: 952

13 Mudryk M. Mąkosza M. Synthesis 1988, 1007

14 Lespagnol A. Cuignet E. Debaert M. Bull. Soc. Chim. Fr. 1960, 383

15 Wittmann H. Ziegler E. Monatsh. Chem. 1988, 119: 103

16 Gustafsson G. Ann. Acad. Sci. Fenn. 1945, 15: 8 ; Chem. Abstr. 1947, 41, 903i

17 Pielichowski J. Popielarz R. Synthesis 1984, 433

18 Smirnova NV. Skoldinov AP. Zh. Org. Khim. 1966, 2: 1261

19 Speziale AJ. Hamm PC. J. Am. Chem. Soc. 1956, 78: 2556

20 Mąkosza M. Kwast A. Tetrahedron 1995, 51: 8339