X=Y−ZH systems as potential 1,3-dipoles. Part 1. background and scope

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue , 1984, Pages 41-46

  Grigg, Ronald ^a   Gunaratne, H Q Nimal ^a   Kemp, James ^a  

^a QUEEN'S UNIVERSITY BELFAST   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049096333     PISSN: 14704358     EISSN: None     Source Type: Journal    
DOI: 10.1039/P19840000041     Document Type: Article

References (61)

1. R. P. Bell, ‘The Proton in Chemistry,’ Cornell University Press, New York, 2nd edn., 1973.
2. R. B. Woodward and R. Hoffmann, ‘The Conservation of Orbital Symmetry,’ Verlag Chemie, Weinheim, Germany, 1970.
3. C. W. Spangler, Chem. Rev., 1976, 76, 187.
4. A. Lapworth, J. Chem. Soc., 1904, 85, 30.
5. J. Klein and S. Brenner, Chem. Commun., 1969, 1020
6. S. Bank, C. A. Rowe, and A. Schriesheim, J. Am. Chem. Soc., 1963, 85, 2115
7. S. Yokoyama, K. Tanaka, and H. Haneda, J. Chem. Soc., Chem. Commun., 1982, 820
8. H. M. Niemeyer and P. Ahlberg, J. Chem. Soc., Chem. Commun., 1974, 799.
9. R. D. Guthrie and J. L. Hedrick, J. Am. Chem. Soc., 1973, 95, 2971.
10. D. A. Jaeger, M. D. Broadhurst, and D. J. Cram, J. Am. Chem. Soc., 1979, 101, 717.
11. H. Dunathan in ‘Advances in Enzymology,’ ed. F. Nord, Wiley, New York, 1971, vol. 35, p. 79
12. A. J. L. Cooper, J. Biol. Chem., 1976, 251, 1088
13. K. R. Hanson and I. A. Rose, Acc. Chem. Res., 1975, 8, 1.
14. K. Vaughan, J. Chem. Soc., Perkin Trans. 2,1977, 17
15. L. Lunazzi, G. Panciera, and M. Guerra, J. Chem. Soc., Perkin Trans, 1980, 2, 52.
16. P. D. Adeney, W. J. Bouma, L. Radom, and W. R. Rodwell, J. Am. Chem. Soc., 1980, 102, 4069
17. Y. Yoshioka and H. F. Schafer, J. Am. Chem. Soc., 1981, 103, 7366 for the effect of orbital population on 1,2-H shifts.
18. K. N. Houk, J. Sims, R. E. Duke, R. W. Strozier, and J. K. George, J. Am. Chem. Soc., 1973, 95, 7287.
19. R. Grigg, J. Kemp, and N. Thompson, Tetrahedron Lett., 1978, 2827.
20. J. Hine, M. S. Cholod, and R. A. King, J. Am. Chem. Soc., 1974, 96, 835
21. E. T. Harper and M. L. Bender, J. Am. Chem. Soc., 1965, 87, 5625
22. R. P. Bell and B. A. Timimi, J. Chem. Soc., Perkin Trans. 2, 1973, 1518
23. T. Okuyama, S. Komoguchi, and T. Fueno, J. Am. Chem. Soc., 1982, 104, 2582
24. S. C. Zimmerman, A. W. Czarnik, and R. Breslow, J. Am. Chem. Soc., 1983, 105, 1694.
25. R. Huisgen, J. Org. Chem., 1976, 41, 403
26. A. Padwa, Angew. Chem., Int. Ed. Engl., 1976, 15, 123
27. W. Oppolzer, Angew. Chem., Int. Ed. Engl., 1977 16, 10
28. R. A. Firestone, Tetrahedron, 1977, 33, 3009.
29. R. Huisgen, Angew. Chem., Int. Ed. Engl., 1963, 2, 565 and 633.
30. R. Huisgen and F. P. Gambra, Tetrahedron Lett., 1982, 23, 55 and earlier papers.
31. W. Bannworth, R. Eidenschink, and T. Kauffmann, Angew. Chem., Int. Ed. Engl., 1974, 13, 468
32. T. Kauffmann, H. Ahlers, A. Hamsen, H. Schulz, H.-J. Tilhard, and A. Vahrenhorst, Angew. Chem., Int. Ed. Engl., 1977, 16, 119.
33. G. Le Fevre, S. Sinbanhit, and J. Hamelin, Tetrahedron, 1979, 35, 1821
34. B. Fouchet, M. Joucla, and J. Hamelin, Tetrahedron Lett., 1981, 22, 1333
35. R. M. Wilson and J. W. Rekers, J. Am. Chem. Soc., 1979, 101, 4005.
36. R. Grigg, M. Jordan, A. Tangthongkum, F. W. B. Einstein, and T. Jones, J. Chem. Soc., Perkin Trans. I, following paper R. Grigg and S. Thianpatanagul, J. Chem. Soc., Perkin Trans. 1, in the press.
37. R. Grigg, M. Jordan, and J. F. Malone, Tetrahedron Lett., 1979, 3877
38. R. Grigg and M. Jordan, unpublished observations.
39. E. H. Cordes and W. P. Jencks, J. Am. Chem. Soc., 1963, 85, 2843
40. J. W. Smith in ‘The Chemistry of the C=N Bond,’ ed. S. Patai, Wiley, 1970, p. 237.
41. M. M. Shemyakin, L. A. Neiman, S. V. Zhukova, Y. S. Nekrasov, T. J. Pehk, and E. T. Lipmaan, Tetrahedron, 1971, 27, 2811.
42. R. Grigg, J. Kemp, G. Sheldrick, and J. Trotter, J. Chem, Soc., Chem. Commun., 1978, 109
43. R. Grigg and V. Sridharan, unpublished results.
44. K. Koch, J.-M. Lin, and F. W. Fowler, Tetrahedron Lett., 1983, 24, 1581.
45. R. Grigg, J. Kemp, J. Malone, and A. Tangthongkum, J. Chem. Soc., Chem. Commun., 1980, 648.
46. K. Amornraksa and R. Grigg, Tetrahedron Lett., 1980, 21, 2197.
47. G. M. Sheldrick and J. Trotter, Acta Crystallogr., Sect. B, 1979, 35, 250.
48. R. Grigg, N. Gunaratne and J. Kemp, in preparation.
49. R. Grigg and H. Q. N. Gunaratne, J. Chem. Soc., Chem. Commun., 1982, 384.
50. R. Grigg and H. Q. N. Gunaratne, Tetrahedron Lett., 1983, 24, 4457.
51. R. Huisgen and K. Herbig, Liebigs Ann. Chem., 1965, 688, 98.
52. R. M. Acheson and B. J. Jones, J. Chem. Soc. C, 1970, 1301.
53. S. T. Murphy, W. C. Taylor, and A. Vadasz, Aust. J. Chem., 1982, 35, 1215.
54. R. Grigg, N. Gunaratne, V. Sridharan, S. Thianpatanagul, and M. Tute, Tetrahedron Lett., 1983 24, 4363.
55. L. Davis and D. E. Metzler in ‘The Enzymes,’ ed. P. D. Boyer, Academic Press, 1972, 3rd edn., vol. 7, ch. 2.
56. R. Grigg and J. Kemp, Tetrahedron Lett., 1978, 31, 2823.
57. R. Grigg and S. Thianpatanagul, unpublished observations.
58. R. Grigg and J. Kemp, J. Chem. Soc., Chem. Commun., 1977, 125.
59. R. Grigg and H. Q. N. Gunaratne, Tetrahedron Lett., 1983, 24, 1201.
60. J. C. Clark, G. H. Phillips, and M. R. Steer, J. Chem. Soc., Perkin Trans. 1, 1976, 475.
61. G. Sunagawa and N. Yoshida, Yakugaku Zasshi, 1962, 82, 841 (Chem. Abstr., 1963, 58, 5650d).