Oxidative nucleophilic substitution of hydrogen in nitroarenes with trifluoromethyl carbanions. Synthesis of trifluoromethyl phenols

Tetrahedron

Volumn 60, Issue 23, 2004, Pages 5019-5024

  Surowiec, Marek ^a   Ma̧kosza, Mieczysław ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

Author keywords

Carbanions; Dimethyldioxirane; Nitroarenes; Phenols; Ruppert reagent

Indexed keywords

AROMATIC NITRO COMPOUND; DIMETHYLDIOXIRANE; HYDROGEN; PHENOL DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; ELECTRON; OXIDATION; PRIORITY JOURNAL; SUBSTITUTION REACTION; SYNTHESIS;

EID: 2442514293     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.04.022     Document Type: Article

References (33)

1. Welch J.T., Eswarakrishnan S. Fluorine in Bioorganic Chemistry. 1991;Wiley, New York
2. Hiyama T. Organofluorine Compounds: Chemistry and Applications. 2000;Springer, Berlin
3. Hudlicky M. Chemistry of Organic Fluorine Compounds I. 2nd ed. 1992;Ellis Horwood, New York. pp 96-106 and 154-158
4. Hudlicky M. Hudlicky M., Pavlath A.E. Chemistry of Organic Fluorine Compounds II. 1995;American Chemical Society, Washington. pp 178-184 and 243-249
5. Baasner B., Hagemann H., Tatlow J.C. Houben-Weyl: Methods of Organic Chemistry. Vol. E10a:1999;Thieme, Stuttgart. Miethchen, R. pp 133-141, 348-370, Yagupolskii, L. M. pp 509-525 and Dmowski, W. pp 321-405
6. Cottet F., Schlosser M. Eur. Org. J. Chem. 2002;327
7. Duan J.-X., Su D.-B., Wu J.-P., Chem Q.-Y. J. Fluorine Chem. 66:1994;167
8. Adams D.J., Clark J.H., Hansen L.B., Sanders V.C., Stewart J.T. J. Chem. Soc. Perkin Trans. 1. 1998;3081
9. Stahly G.P. J. Fluorine Chem. 45:1989;431
10. Terrier F. Chem. Rev. 82:1982;78
11. Terrier F. Nucleophilic Aromatic Displacement. 1991;Chemie, Weinheim
12. Chupakhin O.N., Charushin V.N., van der Plas H.C. Nucleophilic Aromatic Substitution of Hydrogen. 1994;Academic Press, San Diego
13. Makosza M. Russ. Chem. Bull. 45:1996;491
14. Bartoli G. Acc. Chem. Res. 17:1984;109
15. Makosza M., Surowiec M. J. Organometal. Chem. 624:2001;167
16. Makosza M., Winiarski J. Acc. Chem. Res. 20:1987;289
17. Makosza M. Pol. J. Chem. 66:1992;3
18. Makosza M., Wojciechowski K. Liebigs Ann. Recuil. 1997;1805
19. Makosza M., Kwast A. J. Phys. Org. Chem. 11:1998;341
20. Makosza M., Staliński K. Pol. J. Chem. 73:1999;151
21. Makosza M., Staliński K. Chem. Eur. J. 3:1997;2025
22. Makosza M., Staliński K. Synthesis. 1998;1631
23. Makosza M., Staliński K. Tetrahedron. 54:1998;8797
24. Adam W., Makosza M., Staliński K., Zhao C.-G. J. Org. Chem. 63:1998;4390
25. Adam W., Makosza M., Zhao C.-G., Surowiec M. J. Org. Chem. 65:2000;1099
26. Makosza M., Owczarczyk Z. J. Org. Chem. 54:1989;5094
27. Noyori R., Yokoyama K., Sakata J., Kuwajima I., Nakamura E., Shimizu M. J. Am. Chem. Soc. 99:1977;1265
28. Nakamura E., Shimizu M., Kuwajima I., Sakata J., Yokoyama K., Noyori R. J. Org. Chem. 48:1983;932
29. Hine J. Physical Organic Chemistry. 1962;McGraw-Hill, New York. p. 486
30. Epsztajn J., Bieniek A., Brzeziński J.Z., Jóźwiak A. Tetrahedron Lett. 1983;4735
31. Mongin F., Trécomt F., Queguiner G. Terahedron Lett. 1999;5483
32. Adam W., Bialas J., Hadjiarapoglou L. Chem. Ber. 124:1991;2377
33. Gray D.N., Schmidt J.J.E., Smith C.D. J. Chem. Soc. 1960;2243