The influence of nucleophile substituents on the orientation in the reaction between 2,4-difluoronitrobenzene and lithium phenoxides in liquid ammonia

European Journal of Organic Chemistry

Volumn , Issue 2, 2001, Pages 405-411

  Politanskaya, Larisa ^a   Malykhin, Evgenij ^a   Shteingarts, Vitalij ^a  

^a NOVOSIBIRSK STATE UNIVERSITY   (Russian Federation)

Author keywords

2,4 Difluoronitrobenzene; Aromatic nucleophilic substitutions; Liquid ammonia; Lithium phenoxides; Substituent effects in nucleophile

Indexed keywords

2,4 DIFLUORONITROBENZENE; AMMONIA; LITHIUM DERIVATIVE; NITROBENZENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DEFLUORINATION; ELECTRON TRANSPORT; MOLECULAR STABILITY; POLARIZATION; REACTION ANALYSIS; TEMPERATURE DEPENDENCE;

EID: 0035133446     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200101)2001:2<405::AID-EJOC405>3.0.CO;2-6     Document Type: Article

References (33)

1. H. Smith, Organic Reactions in Liquid Ammonia, John Wiley & Sons, New York, 1963, pp. 343.
2. A. A. Shtark, T. A. Kizner, V. D. Shteingarts, Zh. Org. Khim. 1982, 18, 2321-2326.
3. T. A. Kizner, V. D. Shteingarts, Zh. Org. Khim. 1984, 20, 1089-1096.
4. J. F. Bunnet, R. F. Snipes, J. Am. Chem. Soc. 1955, 77, 5422-5433.
5. T. O. Bamkole, J. Hirst, E. I. Udoessien, J. Chem. Soc., Perkin Trans. 2 1973, 2114-2119.
6. B. A. Bolton, J. Miller, V. A. Williams, J. Chem. Soc. 1955, 2926-2929.
7. T. O. Bamkole, J. Hirst, E. I. Udoessien, J. Chem. Soc., Perkin Trans. 2 1973, 110-114.
8. F. Del Cima, G. Biggi, F. Pietra, J. Chem. Soc., Perkin Trans. 2 1973, 55-58.
9. K. R. Plowman, J. J. Lagowski, J. Phys. Chem. 1974, 78, 143-148.
10. A. T. Lemley, J. J. Lagowski, J. Phys. Chem. 1974, 78, 708-713.
11. N. A. Izmailov, Dokl. Akad. Nauk SSSR 1963, 149, 1364-1367.
12. [12a] M. Herlem, A. I. Popov, J. Am. Chem. Soc. 1972, 94, 1431-1434.
13. [12b] W. R. Davidson, P. Kebarle, J. Am. Chem. Soc. 1976, 98, 6133-6138.
14. [12c] B. J. Herold, M. Celina, R. L. R. Lazana, H. M. Novais, Tetrahedron 1977, 33, 517-521.
15. M. Kimura, S. Sekiguchi, K. Matsui, Koguo Kagaku Zasshi 1970, 73, 513-516.
16. L. V. Politanskaya, E. V. Ryabizkaya, E. V. Malykhin, V. D. Shteingarts, Zh. Org. Khim. 2000, 36, 835-841.
17. T. A. Kizner, V. D. Shteingarts, Zh. Org. Khim. 1985, 21, 2376-2382.
18. L. V. Politanskaya, E. V. Malykhin, V. D. Shteingarts, Zh. Org. Khim. 1997, 33, 703-710.
19. L. V. Politanskaya, E. V. Malykhin, V. D. Shteingarts, Zh. Org. Khim. 1996, 32, 1174-1185.
20. R. Bolton, J. P. B. Sandall, J. Chem. Soc., Perkin Trans. 2 1978, 141-144.
21. G. V. L. Bevan, A. F. Foley, J. Hirst, W. O. Uwamu, J. Chem. Soc. B. 1970, 794-797.
22. G. A. Selivanova, T. V. Chuikova, A. A. Shtark, V. D. Shteingarts, Zh. Org. Khim. 1988, 24, 2513-2518.
23. The Sadtler Standard Spectra. Infrared Grating Spectra, Sadtler Research Laboratories, Philadelphia, 1968-1978.
24. R. Silverstein, Spectroscopic identification of organic compounds, Mir, Moscow, 1977, pp. 590.
25. [23a] Y. H. Fendler, W. L. Hinze, L.-J. Liu, J. Chem. Soc., Perkin Trans. 2 1975, 1768-1775.
26. [23b] R. M. Murphy, C. A. Wulff, M. J. Strauss, J. Am. Chem. Soc. 1974, 96, 2678-2682.
27. N. S. Nudelman, P. MacCormack, Tetrahedron 1984, 40, 4227-4235.
28. A. J. Birch, A. L. Hinde, L. Radom, J. Am. Chem. Soc. 1980, 102, 6430-6437.
29. A. A. Bliznyk, A. A. Voityk, Zh. Str. Khim. 1986, 27, 190-191.
30. E. Buncel, R. M. Tarkka, J. M. Dust, Can. J. Chem. 1994, 72, 1709-1721.
31. R. Destro, C. M. Gramaccioli, M. Simonetta, Acta Crystallogr., B 1968, 24, 1369-1386.
32. R. W. Taft, R. D. Topsom, Prog. Phys. Org. Chem. 1987, 16, 1-83.
33. F. Swarts, Recl. Trav. Chim. Pays-Bas 1915, 35, 154-163.