New insight into experimental and theoretical properties of some para-like substituted 2-azidothiophenes

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 3, 1999, Pages 623-627

  Valenti, Francesco ^a   Zanirato, Paolo ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0042134416     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a807350c     Document Type: Article

References (59)

1. Survey articles on this topic have been published: M. Funicello, P. Spagnolo and P. Zanirato, Acta Chem. Scand., 1993, 47, 231; W. Dehaen and J. Becher, Acta Chem. Scand., 1993, 47, 244; D. Spinelli and P. Zanirato, Chem. Ind., (Milan), 1996, 78, 953; T. L. Gilchrist, Adv. Heterocycl. Chem., 1987, 41, 67.
2. Survey articles on this topic have been published: M. Funicello, P. Spagnolo and P. Zanirato, Acta Chem. Scand., 1993, 47, 231; W. Dehaen and J. Becher, Acta Chem. Scand., 1993, 47, 244; D. Spinelli and P. Zanirato, Chem. Ind., (Milan), 1996, 78, 953; T. L. Gilchrist, Adv. Heterocycl. Chem., 1987, 41, 67.
3. Survey articles on this topic have been published: M. Funicello, P. Spagnolo and P. Zanirato, Acta Chem. Scand., 1993, 47, 231; W. Dehaen and J. Becher, Acta Chem. Scand., 1993, 47, 244; D. Spinelli and P. Zanirato, Chem. Ind., (Milan), 1996, 78, 953; T. L. Gilchrist, Adv. Heterocycl. Chem., 1987, 41, 67.
4. Survey articles on this topic have been published: M. Funicello, P. Spagnolo and P. Zanirato, Acta Chem. Scand., 1993, 47, 231; W. Dehaen and J. Becher, Acta Chem. Scand., 1993, 47, 244; D. Spinelli and P. Zanirato, Chem. Ind., (Milan), 1996, 78, 953; T. L. Gilchrist, Adv. Heterocycl. Chem., 1987, 41, 67.
5. For information about the chemistry of heteroaryl azides the reader is referred to the following useful books and reviews: (a) E. F. V. Scriven and K. Turnbull, Chem. Rev., 1988, 88, 297;
6. (b) P. A. S. Smith, Aryl and Heteroaryl Azides and Nitrenes, in Azides and Nitrenes: Reactivity and Utility, E. F. V. Scriven, Academic Press, New York, 1984, pp. 182-193.
7. P. J. Newcombe and R. K. Norris, Tetrahedron Lett., 1981, 22, 699; B. J. Barnes, P. J. Newcombe and R. K. Norris, Aust. J Chem., 1983, 36, 963.
8. P. J. Newcombe and R. K. Norris, Tetrahedron Lett., 1981, 22, 699; B. J. Barnes, P. J. Newcombe and R. K. Norris, Aust. J Chem., 1983, 36, 963.
9. P. A. S. Smith, L. O. Krbechek and W. Reseman, J. Am. Chem. Soc., 1964, 86, 2025; P. A. S. Smith and J. G. Wirth, J. Org. Chem., 1968, 33, 1145.
10. P. A. S. Smith, L. O. Krbechek and W. Reseman, J. Am. Chem. Soc., 1964, 86, 2025; P. A. S. Smith and J. G. Wirth, J. Org. Chem., 1968, 33, 1145.
11. (a) G. L'abbé, L. K. Dyall, K. Meersman and W. Dehaen, J. Chem. Soc., Perkin Trans. 2, 1994, 2401;
12. (b) P. A. S. Smith, G. J. W. Breen, M. K. Hajek and D. V. C. Awang, J. Org. Chem., 1970, 35, 2215.
13. D. Spinelli and P. Zanirato, J. Chem. Soc., Perkin Trans. 2, 1993, 1129.
14. M. Funicello, P. Spagnolo and P. Zanirato, J. Chem. Soc., Perkin Trans. 1, 1990, 2971; M. Toselli, P. Spagnolo and P. Zanirato, Gazz. Chim. Ital., 1989, 119, 411.
15. M. Funicello, P. Spagnolo and P. Zanirato, J. Chem. Soc., Perkin Trans. 1, 1990, 2971; M. Toselli, P. Spagnolo and P. Zanirato, Gazz. Chim. Ital., 1989, 119, 411.
16. S. Gronowitz and P. Zanirato, J. Chem. Soc., Perkin Trans. 2, 1994, 1815.
17. D. Sengupta and M. T. Nguyen, Tetrahedron, 1997, 28, 9647.
18. P. Zanirato, Gazz. Chim. Ital., 1997, 127, 339.
19. (a) M. S. Platz, Acc. Chem. Res., 1995, 28, 487;
20. (b) B. A. Smith and C. J. Cramer, J. Am. Chem. Soc., 1996, 118, 5490;
21. L. K. Dyall, G. L'abbé and W. Dehan, J. Chem. Soc., Perkin Trans. 2, 1997, 971;
22. W. L. Karney and W. Thatcher Borden, J. Am. Chem. Soc., 1997, 119, 1378 and 3347.
23. L. K. Dyall, P. M. Suffolk, W. Dehaen and G. L'abbé, J. Chem. Soc., Perkin Trans. 2, 1994, 2115; E. Ceulemans, K. Vercauteren, L. K. Dyall, D. Buelens and W. Dehaen, Tetrahedron, 1997, 28, 9657; ref. 3.
24. L. K. Dyall, P. M. Suffolk, W. Dehaen and G. L'abbé, J. Chem. Soc., Perkin Trans. 2, 1994, 2115; E. Ceulemans, K. Vercauteren, L. K. Dyall, D. Buelens and W. Dehaen, Tetrahedron, 1997, 28, 9657; ref. 3.
25. D. Davies, P. Spagnolo and P. Zanirato, J. Chem. Soc., Perkin Trans. 1, 1995, 613.
26. P. Spagnolo and P. Zanirato, J. Chem. Soc., Perkin Trans. 1, 1996, 963.
27. (a) C. Hansch, A. Leo and R. W. Taft, Chem. Rev., 1991, 91, 165;
28. (b) M. Charton, Prog. Phys. Org. Chem., 1981, 13, 119;
29. T. H. Lowry and K. Schueller Richardson, Mechanism and Theory in Organic Chemistry, Harper & Row, New York, 1987, p. 143-159;
30. J. March, Advanced Organic Chemistry, J. Wiley, New York, 4th edn., 1992, p. 273.
31. (a) B. Bennetau and J. Dunogues, Synlett, 1992, 171;
32. (b) P. Zanirato, J. Chem. Soc., Perkin Trans. 2, 1991, 2789;
33. P. C. Bulman Page, S. S. Klair and S. Rosenthal, Chem. Soc. Rev., 1990, 19, 147;
34. H. Bock and H. Siedl, J. Organomet. Chem., 1968, 13, 87;
35. (e) P. Magnus and D. Quagliato, J. Org. Chem., 1985, 50, 1621;
36. (f) J. Dunoguès, Bull. Soc., Chim. Fr., 1987, 659.
37. H. Takeuchi, M. Maeda, M. Mitani and K. Kojama, J. Chem. Soc., Chem. Commun., 1985, 287; J. Chem. Soc., Perkin Trans. 1, 1987, 57.
38. H. Takeuchi, M. Maeda, M. Mitani and K. Kojama, J. Chem. Soc., Chem. Commun., 1985, 287; J. Chem. Soc., Perkin Trans. 1, 1987, 57.
39. P. Spagnolo and P. Zanirato, J. Chem. Soc., Perkin Trans. 1, 1988, 2615.
40. F. Valenti, Dr Thesis. University of Bologna, 1997.
41. S. Gronowitz, I. Johnson and A.-B. Hørnfeldt, Chem. Scr., 1975, 7, 76; M. Szaida and J. N. Lam, Thiophenes and their Benzo Derivatives: Structure, in Comprehensive Heterocyclic Chemistry II, A. R. Katritzky, C. W. Rees, E. F. V. Scriven and R. C. Storr, eds. , Pergamon, Oxford, 1996, p. 462.
42. S. Gronowitz, I. Johnson and A.-B. Hørnfeldt, Chem. Scr., 1975, 7, 76; M. Szaida and J. N. Lam, Thiophenes and their Benzo Derivatives: Structure, in Comprehensive Heterocyclic Chemistry II, A. R. Katritzky, C. W. Rees, E. F. V. Scriven and R. C. Storr, eds. , Pergamon, Oxford, 1996, p. 462.
43. R. J. Abraham, J. Fischer and P. Loftus. Introduction to NMR Spectroscopy, J. Wiley, Chichester, 1988; K. Fujieda, K. Takahashi and T. Sone, Bull. Chem. Soc. Jpn., 1985, 58, 1587; W. W. Paudler and M. V. Jovanovic, Org. Magn. Reson., 1982, 19, 192; D. R. Coulson, J. Am. Chem. Soc., 1976, 98, 3111; G. J. Martin, M. L. Martin and S. Odiot, Org. Magn. Reson., 1975, 7, 2; F. Fringuelli, S. Gronowitz, A.-B. Hørnfeldt, I. Johnson and A. Taticchi, Acta Chem. Scand., Ser. B, 1974, 28, 175; J. B. Stothers, Carbon-13 NMR Spectroscopy, Academic Press, New York, ch. 7, 1972, 239; F. Taddei, P. Spagnolo and M. Tiecco, Org. Magn. Reson., 1970, 2, 159; F. J. Weigert and J. D. Roberts, J. Am. Chem. Soc., 1968, 90, 3543; L. M. Jackman, Applications of NMR Spectroscopy to Organic Chemistry, Pergamon, New York, 1959; J. D. Roberts, Nuclear Magnetic Resonance, McGraw-Hill, New York, 1959.
44. R. J. Abraham, J. Fischer and P. Loftus. Introduction to NMR Spectroscopy, J. Wiley, Chichester, 1988; K. Fujieda, K. Takahashi and T. Sone, Bull. Chem. Soc. Jpn., 1985, 58, 1587; W. W. Paudler and M. V. Jovanovic, Org. Magn. Reson., 1982, 19, 192; D. R. Coulson, J. Am. Chem. Soc., 1976, 98, 3111; G. J. Martin, M. L. Martin and S. Odiot, Org. Magn. Reson., 1975, 7, 2; F. Fringuelli, S. Gronowitz, A.-B. Hørnfeldt, I. Johnson and A. Taticchi, Acta Chem. Scand., Ser. B, 1974, 28, 175; J. B. Stothers, Carbon-13 NMR Spectroscopy, Academic Press, New York, ch. 7, 1972, 239; F. Taddei, P. Spagnolo and M. Tiecco, Org. Magn. Reson., 1970, 2, 159; F. J. Weigert and J. D. Roberts, J. Am. Chem. Soc., 1968, 90, 3543; L. M. Jackman, Applications of NMR Spectroscopy to Organic Chemistry, Pergamon, New York, 1959; J. D. Roberts, Nuclear Magnetic Resonance, McGraw-Hill, New York, 1959.
45. R. J. Abraham, J. Fischer and P. Loftus. Introduction to NMR Spectroscopy, J. Wiley, Chichester, 1988; K. Fujieda, K. Takahashi and T. Sone, Bull. Chem. Soc. Jpn., 1985, 58, 1587; W. W. Paudler and M. V. Jovanovic, Org. Magn. Reson., 1982, 19, 192; D. R. Coulson, J. Am. Chem. Soc., 1976, 98, 3111; G. J. Martin, M. L. Martin and S. Odiot, Org. Magn. Reson., 1975, 7, 2; F. Fringuelli, S. Gronowitz, A.-B. Hørnfeldt, I. Johnson and A. Taticchi, Acta Chem. Scand., Ser. B, 1974, 28, 175; J. B. Stothers, Carbon-13 NMR Spectroscopy, Academic Press, New York, ch. 7, 1972, 239; F. Taddei, P. Spagnolo and M. Tiecco, Org. Magn. Reson., 1970, 2, 159; F. J. Weigert and J. D. Roberts, J. Am. Chem. Soc., 1968, 90, 3543; L. M. Jackman, Applications of NMR Spectroscopy to Organic Chemistry, Pergamon, New York, 1959; J. D. Roberts, Nuclear Magnetic Resonance, McGraw-Hill, New York, 1959.
46. R. J. Abraham, J. Fischer and P. Loftus. Introduction to NMR Spectroscopy, J. Wiley, Chichester, 1988; K. Fujieda, K. Takahashi and T. Sone, Bull. Chem. Soc. Jpn., 1985, 58, 1587; W. W. Paudler and M. V. Jovanovic, Org. Magn. Reson., 1982, 19, 192; D. R. Coulson, J. Am. Chem. Soc., 1976, 98, 3111; G. J. Martin, M. L. Martin and S. Odiot, Org. Magn. Reson., 1975, 7, 2; F. Fringuelli, S. Gronowitz, A.-B. Hørnfeldt, I. Johnson and A. Taticchi, Acta Chem. Scand., Ser. B, 1974, 28, 175; J. B. Stothers, Carbon-13 NMR Spectroscopy, Academic Press, New York, ch. 7, 1972, 239; F. Taddei, P. Spagnolo and M. Tiecco, Org. Magn. Reson., 1970, 2, 159; F. J. Weigert and J. D. Roberts, J. Am. Chem. Soc., 1968, 90, 3543; L. M. Jackman, Applications of NMR Spectroscopy to Organic Chemistry, Pergamon, New York, 1959; J. D. Roberts, Nuclear Magnetic Resonance, McGraw-Hill, New York, 1959.
47. R. J. Abraham, J. Fischer and P. Loftus. Introduction to NMR Spectroscopy, J. Wiley, Chichester, 1988; K. Fujieda, K. Takahashi and T. Sone, Bull. Chem. Soc. Jpn., 1985, 58, 1587; W. W. Paudler and M. V. Jovanovic, Org. Magn. Reson., 1982, 19, 192; D. R. Coulson, J. Am. Chem. Soc., 1976, 98, 3111; G. J. Martin, M. L. Martin and S. Odiot, Org. Magn. Reson., 1975, 7, 2; F. Fringuelli, S. Gronowitz, A.-B. Hørnfeldt, I. Johnson and A. Taticchi, Acta Chem. Scand., Ser. B, 1974, 28, 175; J. B. Stothers, Carbon-13 NMR Spectroscopy, Academic Press, New York, ch. 7, 1972, 239; F. Taddei, P. Spagnolo and M. Tiecco, Org. Magn. Reson., 1970, 2, 159; F. J. Weigert and J. D. Roberts, J. Am. Chem. Soc., 1968, 90, 3543; L. M. Jackman, Applications of NMR Spectroscopy to Organic Chemistry, Pergamon, New York, 1959; J. D. Roberts, Nuclear Magnetic Resonance, McGraw-Hill, New York, 1959.
48. R. J. Abraham, J. Fischer and P. Loftus. Introduction to NMR Spectroscopy, J. Wiley, Chichester, 1988; K. Fujieda, K. Takahashi and T. Sone, Bull. Chem. Soc. Jpn., 1985, 58, 1587; W. W. Paudler and M. V. Jovanovic, Org. Magn. Reson., 1982, 19, 192; D. R. Coulson, J. Am. Chem. Soc., 1976, 98, 3111; G. J. Martin, M. L. Martin and S. Odiot, Org. Magn. Reson., 1975, 7, 2; F. Fringuelli, S. Gronowitz, A.-B. Hørnfeldt, I. Johnson and A. Taticchi, Acta Chem. Scand., Ser. B, 1974, 28, 175; J. B. Stothers, Carbon-13 NMR Spectroscopy, Academic Press, New York, ch. 7, 1972, 239; F. Taddei, P. Spagnolo and M. Tiecco, Org. Magn. Reson., 1970, 2, 159; F. J. Weigert and J. D. Roberts, J. Am. Chem. Soc., 1968, 90, 3543; L. M. Jackman, Applications of NMR Spectroscopy to Organic Chemistry, Pergamon, New York, 1959; J. D. Roberts, Nuclear Magnetic Resonance, McGraw-Hill, New York, 1959.
49. R. J. Abraham, J. Fischer and P. Loftus. Introduction to NMR Spectroscopy, J. Wiley, Chichester, 1988; K. Fujieda, K. Takahashi and T. Sone, Bull. Chem. Soc. Jpn., 1985, 58, 1587; W. W. Paudler and M. V. Jovanovic, Org. Magn. Reson., 1982, 19, 192; D. R. Coulson, J. Am. Chem. Soc., 1976, 98, 3111; G. J. Martin, M. L. Martin and S. Odiot, Org. Magn. Reson., 1975, 7, 2; F. Fringuelli, S. Gronowitz, A.-B. Hørnfeldt, I. Johnson and A. Taticchi, Acta Chem. Scand., Ser. B, 1974, 28, 175; J. B. Stothers, Carbon-13 NMR Spectroscopy, Academic Press, New York, ch. 7, 1972, 239; F. Taddei, P. Spagnolo and M. Tiecco, Org. Magn. Reson., 1970, 2, 159; F. J. Weigert and J. D. Roberts, J. Am. Chem. Soc., 1968, 90, 3543; L. M. Jackman, Applications of NMR Spectroscopy to Organic Chemistry, Pergamon, New York, 1959; J. D. Roberts, Nuclear Magnetic Resonance, McGraw-Hill, New York, 1959.
50. R. J. Abraham, J. Fischer and P. Loftus. Introduction to NMR Spectroscopy, J. Wiley, Chichester, 1988; K. Fujieda, K. Takahashi and T. Sone, Bull. Chem. Soc. Jpn., 1985, 58, 1587; W. W. Paudler and M. V. Jovanovic, Org. Magn. Reson., 1982, 19, 192; D. R. Coulson, J. Am. Chem. Soc., 1976, 98, 3111; G. J. Martin, M. L. Martin and S. Odiot, Org. Magn. Reson., 1975, 7, 2; F. Fringuelli, S. Gronowitz, A.-B. Hørnfeldt, I. Johnson and A. Taticchi, Acta Chem. Scand., Ser. B, 1974, 28, 175; J. B. Stothers, Carbon-13 NMR Spectroscopy, Academic Press, New York, ch. 7, 1972, 239; F. Taddei, P. Spagnolo and M. Tiecco, Org. Magn. Reson., 1970, 2, 159; F. J. Weigert and J. D. Roberts, J. Am. Chem. Soc., 1968, 90, 3543; L. M. Jackman, Applications of NMR Spectroscopy to Organic Chemistry, Pergamon, New York, 1959; J. D. Roberts, Nuclear Magnetic Resonance, McGraw-Hill, New York, 1959.
51. R. J. Abraham, J. Fischer and P. Loftus. Introduction to NMR Spectroscopy, J. Wiley, Chichester, 1988; K. Fujieda, K. Takahashi and T. Sone, Bull. Chem. Soc. Jpn., 1985, 58, 1587; W. W. Paudler and M. V. Jovanovic, Org. Magn. Reson., 1982, 19, 192; D. R. Coulson, J. Am. Chem. Soc., 1976, 98, 3111; G. J. Martin, M. L. Martin and S. Odiot, Org. Magn. Reson., 1975, 7, 2; F. Fringuelli, S. Gronowitz, A.-B. Hørnfeldt, I. Johnson and A. Taticchi, Acta Chem. Scand., Ser. B, 1974, 28, 175; J. B. Stothers, Carbon-13 NMR Spectroscopy, Academic Press, New York, ch. 7, 1972, 239; F. Taddei, P. Spagnolo and M. Tiecco, Org. Magn. Reson., 1970, 2, 159; F. J. Weigert and J. D. Roberts, J. Am. Chem. Soc., 1968, 90, 3543; L. M. Jackman, Applications of NMR Spectroscopy to Organic Chemistry, Pergamon, New York, 1959; J. D. Roberts, Nuclear Magnetic Resonance, McGraw-Hill, New York, 1959.
52. R. J. Abraham, J. Fischer and P. Loftus. Introduction to NMR Spectroscopy, J. Wiley, Chichester, 1988; K. Fujieda, K. Takahashi and T. Sone, Bull. Chem. Soc. Jpn., 1985, 58, 1587; W. W. Paudler and M. V. Jovanovic, Org. Magn. Reson., 1982, 19, 192; D. R. Coulson, J. Am. Chem. Soc., 1976, 98, 3111; G. J. Martin, M. L. Martin and S. Odiot, Org. Magn. Reson., 1975, 7, 2; F. Fringuelli, S. Gronowitz, A.-B. Hørnfeldt, I. Johnson and A. Taticchi, Acta Chem. Scand., Ser. B, 1974, 28, 175; J. B. Stothers, Carbon-13 NMR Spectroscopy, Academic Press, New York, ch. 7, 1972, 239; F. Taddei, P. Spagnolo and M. Tiecco, Org. Magn. Reson., 1970, 2, 159; F. J. Weigert and J. D. Roberts, J. Am. Chem. Soc., 1968, 90, 3543; L. M. Jackman, Applications of NMR Spectroscopy to Organic Chemistry, Pergamon, New York, 1959; J. D. Roberts, Nuclear Magnetic Resonance, McGraw-Hill, New York, 1959.
53. R. J. Abraham, J. Fischer and P. Loftus. Introduction to NMR Spectroscopy, J. Wiley, Chichester, 1988; K. Fujieda, K. Takahashi and T. Sone, Bull. Chem. Soc. Jpn., 1985, 58, 1587; W. W. Paudler and M. V. Jovanovic, Org. Magn. Reson., 1982, 19, 192; D. R. Coulson, J. Am. Chem. Soc., 1976, 98, 3111; G. J. Martin, M. L. Martin and S. Odiot, Org. Magn. Reson., 1975, 7, 2; F. Fringuelli, S. Gronowitz, A.-B. Hørnfeldt, I. Johnson and A. Taticchi, Acta Chem. Scand., Ser. B, 1974, 28, 175; J. B. Stothers, Carbon-13 NMR Spectroscopy, Academic Press, New York, ch. 7, 1972, 239; F. Taddei, P. Spagnolo and M. Tiecco, Org. Magn. Reson., 1970, 2, 159; F. J. Weigert and J. D. Roberts, J. Am. Chem. Soc., 1968, 90, 3543; L. M. Jackman, Applications of NMR Spectroscopy to Organic Chemistry, Pergamon, New York, 1959; J. D. Roberts, Nuclear Magnetic Resonance, McGraw-Hill, New York, 1959.
54. Wavefunction, Irvine, 1996; W. J. Hehre and W. W. Huang, Chemistry with computation, Wavefunction, Irvine, 1995.
55. M. J. S. Dewar, E. G. Zoebisch, E. F. Healy and J. J. P. Stewart, J. Am. Chem. Soc., 1985, 107, 3902.
56. W. J. Hehre, L. Radom, J. A. Pople and P. v. R. Schleyer, Ab initio Molecular Orbital Theory, J. Wiley, New York, 1986; P. C. Hariharan and J. A. Pople, Theor. Chim. Acta. 1973, 28, 213.
57. W. J. Hehre, L. Radom, J. A. Pople and P. v. R. Schleyer, Ab initio Molecular Orbital Theory, J. Wiley, New York, 1986; P. C. Hariharan and J. A. Pople, Theor. Chim. Acta. 1973, 28, 213.
58. R. Herges, Angew. Chem., Int. Ed. Engl. 1994, 33, 255.
59. M. J. Pilling and P. W. Seakins, Reaction Kinetics, Oxford University Press, 1996.