The synthesis and reactivity of 5H-cycloprop[f]isobenzofuran and related compounds. A kinetic probe for the mills-nixon effect

Australian Journal of Chemistry

Volumn 49, Issue 12, 1996, Pages 1263-1272

  Anthony, Ian J ^a   Wege, Dieter ^a  

^a UNIVERSITY OF WESTERN AUSTRALIA   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0005751592     PISSN: 00049425     EISSN: None     Source Type: Journal    
DOI: 10.1071/CH9961263     Document Type: Article

References (62)

1. Friedrichsen, W., Adv. Heterocycl. Chem., 1980, 26, 135.
2. Wiersum, U. F., Aldrichimica Acta, 1981, 14, 53.
3. Rickborn, B., in 'Advances in Theoretically Interesting Molecules' (Ed. R. P. Thummel) Vol. 1, p. 1 (JAI Press: Greenwich, Connecticut, 1989).
4. Rodrigo, R., Tetrahedron, 1988, 44, 2093.
5. Friedrichsen, W., in Houben-Weyl 'Methoden der organischen Chemie' (Ed. R. P. Kreher) Vol. E6b1, p. 163 (Georg Thieme: Stuttgart 1994).
6. Moursounidis, J., and Wege, D., Aust. J. Chem., 1988, 41, 235.
7. Halton, B., Chem, Rev., 1973, 73, 113.
8. Billups, W. E., Acc. Chem. Res., 1978, 11, 245.
9. Halton, B., Ind. Eng. Chem. Prod. Res. Dev., 1980, 19, 349.
10. Billups, W. E., Rodin, W. A., and Haley, M. M., Tetrahedron, 1988, 44, 1305.
11. Halton, B., Chem. Rev., 1989, 89, 1161.
12. Tanimoto, S., Schäfer, R., Ippen, J., and Vogel, E., Angew. Chem., Int. Ed. Engl., 1976, 15, 613.
13. Halton, B., Dent, B. R., Böhm, S., Officer, D. L., Schmückler, H., Schophoff, F., and Vogel, E., J. Am. Chem. Soc., 1985, 107, 7175.
14. Dent., B. R., and Halton., B., Aust. J. Chem., 1987, 40, 925.
15. Mills, W. H., and Nixon, I. G., J. Chem. Soc., 1930, 2510.
16. For example: Hiberty, P. C., Ohanessian, G., and Delbecq, F., J. Am. Chem. Soc., 1985, 107, 3095;
17. Apeloig, Y., and Arad, D., J. Am. Chem. Soc., 1986, 108, 3241;
18. Collins, M. J., Gready, J. E., Sternhell, S., and Tansey, C., Aust. J. Chem., 1990, 43, 1547;
19. Davies, A. G., and Ng, K. M., J. Chem. Soc., Perkin Trans. 2, 1992, 1857;
20. Stanger, A., J. Am. Chem. Soc., 1991, 113, 8277;
21. Baldridge, K. K., and Siegel, J. S., J. Am. Chem. Soc., 1992, 114, 9583;
22. Mitchell, R. H., and Lau, D. Y. K., Tetrahedron Lett, 1995, 51, 9281;
23. Mitchell, R. H., Chen, Y., Iyer, S. V., Lau, D. Y. K., Baldridge, K. K., and Siegel, J. S., J. Am. Chem. Soc., 1996, 118, 2907.
24. Siegel, J. S., Angew. Chem., Int. Ed. Engl., 1994, 33, 1721.
25. Neidlein, R., Christen, D., Poignée, V., Boese, R., Bläser, D., Gieren, A., Ruiz-Pérez, C., and Hübner, T., Angew. Chem., Int. Ed. Engl., 1988, 27, 294.
26. Boese, R., and Bläser, D., Angew. Chem., Int. Ed. Engl., 1988, 27, 304.
27. Boese, R., Bläser, D., Billups, W. E., Haley, M. M., Maulitz, A. H., Mohler, D. L., and Vollhardt, K. P. C., Angew. Chem., Int. Ed. Engl., 1994, 33, 313.
28. Mó, O., Yáñez, M., Eckert-Maksic, M., and Maksic, Z. B., J. Org. Chem., 1995, 60, 1638.
29. Anthony, I. J., and Wege, D., Tetrahedron Lett., 1987, 28, 4217.
30. Dent, B. R., Halton., B., and Smith, A. M. F., Aust. J. Chem., 1986, 39, 1621.
31. Gaoni, Y., and Sadeh, S., J. Org. Chem., 1980, 45, 870.
32. Bambal, R., Fritz, H., Rihs, G., Tschamber, T., and Streith, J., Angew. Chem., Int. Ed. Engl., 1987, 26, 668.
33. Buckland, S. J., Halton, B., and Stanovnik, B., Aust. J. Chem., 1987, 40, 2037.
34. Müller, P., and Schaller, J.-P., Tetrahedron Lett., 1989, 30, 1507; Helv. Chim. Acta, 1989, 72, 1608.
35. Müller, P., and Schaller, J.-P., Tetrahedron Lett., 1989, 30, 1507; Helv. Chim. Acta, 1989, 72, 1608.
36. Anthony, I. J., Kang., Y. B., and Wege, D., Tetrahedron Lett, 1990, 31, 1315.
37. Müller, P., and Miao, Z., Helv. Chim. Acta, 1994, 77, 1826.
38. Cauberé, P., Acc. Chem. Res., 1974, 7, 301.
39. Halton, B., and Randall, C. J., J. Am. Chem. Soc., 1983, 105, 6310; Apeloig, Y., Arad, D., Halton, B., and Randall, C. J., J. Am. Chem. Soc., 1986, 108, 4932.
40. Halton, B., and Randall, C. J., J. Am. Chem. Soc., 1983, 105, 6310; Apeloig, Y., Arad, D., Halton, B., and Randall, C. J., J. Am. Chem. Soc., 1986, 108, 4932.
41. Finnegan, R. A., J. Org. Chem., 1965, 30, 1333.
42. Streitwieser, A., Jr, Ziegler, G. R., Mowery, P. C., Lewis, A., and Lawler, R. G., J. Am. Chem. Soc., 1968, 90, 1357.
43. Streitwieser, A., Jr, Young, W. R., and Caldwell, R. A., J. Am. Chem. Soc., 1969, 91, 527; Streitwieser, A., Jr, Caldwell, R. A., and Young, W. R., J. Am. Chem. Soc., 1969, 91, 529.
44. Streitwieser, A., Jr, Young, W. R., and Caldwell, R. A., J. Am. Chem. Soc., 1969, 91, 527; Streitwieser, A., Jr, Caldwell, R. A., and Young, W. R., J. Am. Chem. Soc., 1969, 91, 529.
45. Garrat, P. J., and Koller, W., Tetrahedron Lett., 1976, 4177.
46. Breitmaier, E., and Voelter, W., '13C N.M.R.-Spectroscopy' p. 93 (Verlag Chemie: Weinheim 1974).
47. Wilson, W. S., and Warrener, R. N., J. Chem. Soc., Chem. Commun., 1972, 211.
48. Buttery, J. H., Moursounidis, J., and Wege, D., Aust. J. Chem., 1995, 48, 593.
49. Swain, C. G., J. Org. Chem., 1984, 49, 2005.
50. Stirling, C. J. M., Tetrahedron, 1985, 41, 1613.
51. Hamon, D. G. P., and Spurr, P. R., Synthesis, 1981, 873.
52. Lloyd, J. B. F., and Ongley, P. A., Tetrahedron, 1965, 21, 245.
53. Hillard, R. L., III, and Vollhard, K. P. C., Angew. Chem., Int. Ed. Engl., 1977, 16, 399.
54. Eigenmann, G., and Zollinger, H., Helv. Chim. Acta, 1965, 48, 1795.
55. Wisansky, W. A., and Ansbacher S., Org. Synth., 1955, Collect. Vol. 3, 138.
56. Klingsberg, E., Synthesis, 1972, 29.
57. Barton, J. W., Shepherd, M. K., and Wills, R. J., J. Chem. Soc., Perkin Trans. 1, 1986, 967.
58. Aalbersberg, W. G. L., Barkovich, A. J., Funk, R. L., Hillard, R. L., III, and Vollhardt, K. P. C., J. Am. Chem. Soc., 1975, 97, 5600.
59. Hillard, R. L., III, and Vollhardt, K. P. C., J. Am. Chem. Soc., 1976, 98, 3579.
60. Wolthuis, E., J. Org. Chem., 1961, 26, 2215.
61. Hart, H., Bashir-Hashemi, A., Luo, J., and Meador, M. A., Tetrahedron, 1986, 42, 1641.
62. Wege, D., Tetrahedron Lett., 1971, 2337.