Nucleophilic substitutions at the pyridine ring. Conformational preference of the products and kinetics of the reactions of 2-chloro-3-nitro- and 2-chloro-5-nitro-pyridines with arenethiolates

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 11, 1997, Pages 2415-2421

  Hamed, Ezzat A ^a   El Bardan, Ali A ^a   Saad, Esmat F ^b   Gohar, Gamal A ^a   Hassan, Ghada M ^a  

^a Alexandria University Faculty Of Science   (Egypt)

^b Alexandria University   (Egypt)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001745498     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a701902e     Document Type: Article

References (40)

1. (a) F. Terrier, Nucleophilic Aromatic Displacements. The Influence of the Nitro Group, VCH, New York, 1991;
2. (b) E. Buncel, M. R. Crampton, M. J. Strauss and F. Terrier, Electron Deficient Aromatic and Heteroaromatic Anionic Sigma Complexes, Elsevier, Amsterdam, 1984.
3. J. Miller, Aromatic Nucleophilic Substitution, Elsevier, Amsterdam, 1968.
4. M. R. Crampton, Organic Reaction Mechanisms 1994, ed. C. A. Knipe and W. E. Watts, John Wiley, New York, 1996.
5. (a) C. Arnone, G. Consiglio and D. Spinelli, J. Chem. Soc., Perkin Trans. 2, 1989, 1609 and references cited therein;
6. (b) C. Doddi, G. Illuminati, P. Mencarelli and F. Stegel, J. Org. Chem., 1976, 41, 2825;
7. (c) G. Illuminati and F. Stegel, Adv. Heterocycl. Chem., 1983, 34, 305.
8. D. M. Brewis, N. B. Chapman, J. S. Paine, J. Shorter and D. J. Wright, J. Chem. Soc., Perkin Trans. 2, 1974, 1787.
9. A. R. Katritzky, Adv. Heterocycl. Chem., 1964, 3, 309.
10. (a) H. H. Jaffe and H. L. Jones, Adv. Heterocycl. Chem., 1964, 3, 209;
11. (b) G. R. Newkome and W. W. Paudler, Contemporary Heterocyclic Chemistry, John Wiley & Sons, New York, 1982.
12. P. Bemporad, G. Illuminati and F. Stegel, J. Am. Chem. Soc., 1969, 91, 6742 and references therein.
13. (a) E. F. Saad, A. A. El-Bardan and E. A. Hamed, Spectrosc. Lett., 1990, 23, 1347;
14. (b) E. A. Hamed, A. El-Faham, E. F. Saad and A. A. El-Bardan, Phosphorus, Sulfur Silicon Relat. Elem., 1997, 119, 11.
15. G. Motaudo, P. Finocchiaro, E. Trevillone and P. Maravigna, Tetrahedron, 1971, 27, 2125.
16. G. Montaudo, P. Finocchiaro and S. Caccamese, J. Org. Chem., 1971, 36, 2860.
17. (a) G. Montaudo, F. Bottino and E. Trevillone, J. Org. Chem., 1971, 37, 504;
18. (b) S. Oae, Organic Sulfur Chemistry: Structure and Mechanism, CRC Press, New York, 1991, ch. 2.
19. A. A. El-Bardan, N. M. El-Mallah and E. A. Hamed, J. Phys. Org. Chem., 1992, 5, 239.
20. N. Goodhand and T. A. Hamor, J. Fluorine Chem., 1990, 48, 45.
21. G. Montaudo and P. Finocchiaro, J. Am. Chem. Soc., 1972, 94, 6745 and references therein.
22. G. Montaudo, P. Maravigna and P. Finocchiaro, J. Mol. Struct., 1972, 13, 309; 1972, 14, 53.
23. G. Montaudo, P. Maravigna and P. Finocchiaro, J. Mol. Struct., 1972, 13, 309; 1972, 14, 53.
24. G. Montaudo, S. Caccamese, P. Finocchiaro and F. Bottino, Bull. Chem. Soc. Jpn., 1971, 44, 1439.
25. P. A. Lehmann F, Tetrahedron, 1997, 30, 719.
26. C. E. Johnson and F. A. Bovey, J. Chem. Phys., 1958, 29, 1012.
27. E. A. Hamed, A. A. El-Bardan, G. A. Gohar and A. N. Asaad, Spectrosc. Lett., 1996, 29, 549.
28. J. D. Korp, I. Bernal and G. E. Martin, J. Cryst. Mol. Struct., 1981, II (1/2), 11.
29. J. F. Bunnett and R. F. Snipes, J. Am. Chem. Soc., 1955, 77, 5422.
30. J. E. Bunnett and W. D. Merritt, Jr, J. Am. Chem. Soc., 1957, 79, 5967.
31. T. L. Gilchrist, Heterocyclic Chemistry, 2nd edn., John Wiley & Sons, New York, 1992.
32. M. R. Crampton and M. J. Willison, J. Chem. Soc., Perkin Trans. 2, 1974, 238.
33. (a) G. Illuminati, Adv. Heterocycl. Chem., 1964, 3, 285;
34. (b) A. D. Dumm and R. Norrie, J. Heterocycl. Chem., 1987, 24, 85;
35. (c) T. A. Emokape, P. U. Uwakwe and J. Hirst, J. Chem. Soc., Perkin Trans. 2, 1993, 125.
36. T. Tsuno, T. Ibata and Y. Yukawa, Bull. Chem. Soc. Jpn., 1959, 32, 965.
37. R. Taft and I. C. Lewis, J. Am. Chem. Soc., 1959, 81, 5343.
38. M. R. Crampton, J. Chem. Soc. (B), 1971, 2112.
39. L. Forlani, G. Bartoli and P. E. Todesco, Int. J. Sulfur Chem., Part C, 1971, 6, 77.
40. E. A. Hamed, Int. J. Chem. Kinet., 1997, 26, 515.