Synthesis and Diatropicity of trans-N-Cyclohexyl-2′,5′,10b,10c-tetramethyl-pyrrolo[3,4-e]-10b,10c- dihydropyrene. the First Example of an Iso[17]annulenopyrrole

Journal of Organic Chemistry

Volumn 62, Issue 17, 1997, Pages 6060-6063

  Lai, Yee Hing ^a   Chen, Pu ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

ANNULENE DERIVATIVE; FURAN DERIVATIVE; PYRROLE DERIVATIVE;

AROMATIZATION; ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; MOLECULAR INTERACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0030833256     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970430g     Document Type: Article

References (62)

1. (a) Garratt, P. J. Aromaticity; Wiley: New York, 1986.
2. (b) Badger, G. M. Aromatic Character and Aromaticity, University Press: Cambridge, 1969.
3. (a) Balaban, A. T. Pure Appl. Chem. 1980, 52, 1409.
4. (b) Gorelik, M. V. Russ. Chem. Rev. 1990, 59, 116.
5. Balaban, A. T.; Banciu, M.; Ciorba, V. Annulene, Benzo-, Hetero-, Homo-Derivatives, and Their Valence Isomers; CRC Press Inc.: Boca Raton, FL, 1987; Vols. 1-3.
6. (a) Katritzky, A. R.; Lagowski, J. M. The Principles of Heterocyclic Chemistry; Chapman and Hall Ltd.: London, 1967.
7. (b) Kellogg, R. M. In Comprehensive Heterocyclic Chemistry; Bird, C. W., Cheeseman, G. W. H., Eds.; Pergamon Press: Oxford, 1984; Vol. 4, Part 3.
8. Cook, M. J.; Katritzky, A. R.; Linda, P. Adv. Heterocycl. Chem. 1974, 17, 255.
9. (a) George, P.; Bock, C. W.; Trachtman, M. Tetrahedron Lett. 1985, 26, 5667.
10. (b) Bedford, A. F.; Beezer, A. E.; Mortimer, C. T. J. Chem. Soc. 1963, 2039.
11. (c) Guthrie, G. B.; Scott, D. W.; Hubbard, W. N.; Katz, C.; McCollough, J. P.; Gross, M. E.; Williamson, K. D.; Waddington, G. J. Am. Chem. Soc. 1952, 74, 4662.
12. (a) Bird, C. W. Tetrahedron 1992, 48, 335.
13. (b) Bird, C. W. Tetrahedron 1986, 42, 89;
14. (c) Tetrahedron 1985, 41, 1409.
15. (a) Katritzky, A. R.; Karelson, M.; Malhotra, N. Heterocycles 1991, 32, 127.
16. (b) Katritzky, A. R.; Barczynski, P.; Musumarra, G.; Pisano, D.; Szafran, M. J. Am. Chem. Soc. 1989, 111, 7.
17. (a) Vollhardt, K. P. C.; Bergman, R. G. J. Am. Chem. Soc. 1972, 94, 8950.
18. (b) LeGoff, E.; LaCount, R. B. Tetrahedron Lett. 1965, 2787.
19. (c) Warrener, R. N. J. Am. Chem. Soc. 1971, 93, 2346.
20. (d) Wege, D. Tetrahedron Lett. 1971, 2337.
21. (e) Wiersum, U. E.; Mijs, W. J. J. Chem. Soc., Chem. Commun. 1972, 347.
22. Junic, A.; Sabljic, A.; Trinajstic, N. J. Heterocycl. Chem. 1984, 21, 273.
23. This term is derived qualitatively from isobenzofuran, isobenzothiophene and isobenzopyrrole.
24. (a) Beeby, P. J.; Weavers, R. T.; Sondheimer, F. Angew. Chem., Int. Ed. Engl. 1974, 13, 138.
25. (b) Cresp, T. M.; Sondheimer, F. J. Am. Chem. Soc. 1975, 97, 4412.
26. Jones, R. R.; Brown, J. M.; Sondheimer, F. Tetrahedron Lett. 1975, 4183.
27. (a) Ebe, H.; Nakagawa, T.; Iyoda, M.; Nagakawa, M. Tetrahedron Lett. 1981, 22, 4441.
28. (b) Iyoda, M.; Nagakawa, T.; Ebe, H.; Oda, M.; Nakagawa, M.; Yamamoto, K.; Higuchi, H.; Ojima, J. Bull. Chem. Soc. Jpn. 1994, 67, 778.
29. (a) Mitchell, R. H.; Zhou, P. Tetrahedron Lett. 1991, 32, 6319.
30. (b) Mitchell, R. H.; Iyer, V. S.; Khalifa, N.; Mahadevan, R.; Venugopalan, S.; Weerawarna, S. A.; Zhou, P. J. Am. Chem. Soc. 1995, 117, 1514.
31. Lai, Y.-H.; Chen, P. J. Org. Chem. 1996, 61, 935.
32. (a) Whitesides, G. M.; Pawson, B. A.; Cope, A. C. J. Am. Chem. Soc. 1968, 90, 639.
33. (b) Cram, D. J.; Montgomery, C. S.; Knox, G. R. J. Am. Chem. Soc. 1966, 88, 515.
34. (c) Haley, J. F., Jr.; Resenfeld, S. M.; Keehn, P. M. J. Org. Chem. 1977, 42, 1379.
35. (d) Lee, A. W.; Keehn, P. M.; Ramos, S. M.; Rosenfeld, S. M. Heterocycles 1977, 7, 81.
36. (e) Marcel, S. F.; Lie, J. K.; Fasih, A. J. Chem. Soc., Chem. Commun. 1981, 1110.
37. (f) Rosenfeld, S. M.; Sanford, E. M. Tetrahedron Lett. 1987, 4775. J. Am. Chem. Soc. 1968, 90, 639.
38. (f) Rosenfeld, S. M.; Sanford, E. M. Tetrahedron Lett. 1987, 4775. J. Am. Chem. Soc. 1968, 90, 639.
39. (a) Allen, G. F. H.; Gates, J. W., Jr. J. Am. Chem. Soc. 1943, 65, 1283.
40. (b) Cava, M. P.; Scheel, F. M. J. Org. Chem. 1967, 32, 1304.
41. (c) Garratt, P. J.; Neoh, S. B. J. Org. Chem. 1975, 40, 970.
42. (a) Mukaiyama, T.; Hata T. Bull. Chem. Soc. Jpn. 1961, 43, 99.
43. (b) Nozaki, N.; Koyama, T.; Mori, T. Tetrahedron 1969, 25, 5357.
44. New, M. S. Organic Syntheses; Wiley: New York, 1955; Collect. Vol. III, p 631.
45. (a) Rossa, L.; Vögtle, F. Top. Curr. Chem. 1983, 113, 1.
46. (b) Knops, P.; Sendhoff, N.; Mekelburger, H.-B.; Vögtle, F. Ibid. 1991, 161, 1.
47. (c) Ostrowicki, A.; Koepp, E. Vögtle, F. Ibid. 1991, 161, 37.
48. Mitchell, R. H.; Yan, J. S. H. Can. J. Chem. 1980, 58, 2584.
49. (a) Lai, Y.-H. J. Chem. Soc., Perkin Trans. 2 1986, 1667.
50. (b) Oki, M. Applications of Dynamic NMR Spectroscopy to Organic Chemistry; VCH Publishers: Deerfield Beach, FL, 1985.
51. (c) Calder, I. C.; Garratt, P. J. J. Chem. Soc. B 1967, 660.
52. (d) Kessler, H. Angew. Chem., Int. Ed. Engl. 1970, 9, 219.
53. (e) Gygax, R.; Wirz, J.; Sprague, J. T.; Allinger, N. L. Helv. Chim. Acta 1977, 60, 2522.
54. (f) Hutton, H. H.; Hiebert, W. E.; Mark, V. Can. J. Chem. 1978, 56, 1261.
55. See, for example: (a) Barlow, M. G.; Hazeldine, R. N.; Hubbard, R. J. Chem. Soc., Chem. Commun. 1966, 143. (b) Wittig, G.; Beichel, B. Chem. Ber. 1963, 96, 2851.
56. See, for example: (a) Barlow, M. G.; Hazeldine, R. N.; Hubbard, R. J. Chem. Soc., Chem. Commun. 1966, 143. (b) Wittig, G.; Beichel, B. Chem. Ber. 1963, 96, 2851.
57. White, J. D.; Mann, M. E. Adv. Heterocycl. Chem. 1969, 10, 113.
58. Mitchell, R. H.; Boekelheide, V. J. Am. Chem. Soc. 1974, 96, 1547.
59. Boekelheide, V.; Phillips, J. B. J. Am. Chem. Soc. 1967, 89, 1695.
60. Mitchell, R. H.; Yan, J. S. H. Can. J. Chem. 1977, 55, 3347.
61. 22 series.
62. 16 series.