Photoinduced reactions of chloranil with 1,1-diarylethenes and product photochemistry-intramolecular [2 + 2] (ortho-)cycloadditions of excited enedione's C=C double bond with substituted benzene ring

Journal of Organic Chemistry

Volumn 65, Issue 1, 2000, Pages 30-40

  Xue, Jie ^a   Xu, Jian Wei ^a   Yang, Li ^b   Xu, Jian Hua ^a  

^a NANJING UNIVERSITY   (China)

^b LANZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; CHLORANIL; ETHYLENE DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ELECTRON TRANSPORT; HYDROPHILICITY; OXIDATION; PHOTOCHEMISTRY; REACTION ANALYSIS;

EID: 0033963524     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990831r     Document Type: Article

References (82)

1. (a) Bruce, J. M. Photochemistry of Quinones. In The Chemistry of Quinoid Compounds; Patai, S., Ed.; Wiley: New York, 1974; Part 1.
2. (b) Maruyama, K.; Osuka, A. Recent Advances in the Photochemistry of Quinones. In The Chemistry of Quinoid Compounds; Patai, S., Rappoport, Z., Ed.; Wiley: New York, 1988; Part 2.
3. Bryth-Smith, D.; Evans, E. H.; Gilbert, A.; McNeill, H. S. J. Chem. Soc., Perkin Trans. 2 1991, 1587; J. Chem. Soc., Perkin Trans. 1 1992, 485.
4. Bryth-Smith, D.; Evans, E. H.; Gilbert, A.; McNeill, H. S. J. Chem. Soc., Perkin Trans. 2 1991, 1587; J. Chem. Soc., Perkin Trans. 1 1992, 485.
5. Schenk, G. O. Z. Electrochem. 1960, 64, 997.
6. Bryce-Smith, D.; Gilbert, A. Tetrahedron Lett. 1964, 3471.
7. Barltrop, J. A.; Hesp, B. J. Chem. Soc., C 1967, 1625.
8. Ogino, K.; Matsumato, T.; Kozuka, S. J. Chem. Soc., Chem. Commun. 1979, 643.
9. (a) Roth, H. D.; Albert, C. J. J. Am. Chem. Soc. 1986, 108, 2013.
10. (b) Miyashi, T.; Konno, A.; Takahashi, Y.; Kaneko, A.; Suzuki, T.; Mukai, T. Tetrahedron Lett. 1989, 30, 5297.
11. Christal, V. M.; Braun, M. Angew. Chem. 1989, 101, 636.
12. Jones, G., II; Haney, W. A. J. Phys. Chem. 1986, 90, 5410.
13. (a) Rentzepis, P. M.; Steyert, D. W.; Roth, H. D.; Albert, C. J. J. Phys. Chem. 1985, 89, 3955.
14. (b) Miyashi, T.; Takahashi, Y.; Mukai, T.; Roth, H. D.; Schilling, M. L. M. J. Am. Chem. Soc. 1985, 107, 1079.
15. (a) Oshima, T.; Nagai, T. Bull. Chem. Soc. Jpn. 1980, 53, 726.
16. (b) Tanura, H.; Oshima, T.; Nagai, T.; Inaba, A.; Chihara, H. Acta Crystallogr., Sect. 3, Struct. Commun. 1996, 46, 609.
17. Eckert, G.; Goez, M. J. Am. Chem. Soc. 1994, 116, 11999.
18. (a) Xu, J. H.; Wang, L. C.; Xu, J. W.; Yan, B. Z.; Yuan, H. C. J. Chem. Soc., Perkin Trans. 1 1994, 571.
19. (b) Xu, J. H.; Song, Y. L.; Zhang, Z. G.; Wang, L. C.; Xu, J. W. Tetrahedron 1994, 50, 1199.
20. 16 The reduction potential of the triplet excited state is 2.14 V (SCE).
21. (a) Peover, M. E. Nature (London) 1961, 191, 702.
22. (b) Mann, C. K.; Barnes, K. K. Electrochemical Reactions in Nonaqueous Systems; Delaker: New York, 1970.
23. Gschwind, R.; Haselback, E. Helv. Chim. Acta 1979, 62, 941.
24. Weller, A. Z. Phys. Chem. (Wiesbaden) 1982, 133, 193.
25. (a) Chen, C. F.; Zhang, Z. G.; Yan, B. Z.; Xu, J. H. Tetrahedron Lett. 1994, 35, 9221.
26. (b) Yan, B. Z.; Zhang, Z. G.; Yuan, H. C.; Wang, L. C.; Xu, J. H. J. Chem. Soc., Perkin Trans. 2 1994, 2545.
27. (c) Xu, J. H.; Xu, J. W.; Yan, B. Z.; Yuan, H. C. Chinese Chem. Lett. 1991, 2, 831.
28. Benesi, H. G.; Hildebrand, J. H. J. Am. Chem. Soc. 1947, 71, 2703.
29. (a) Foster, R. In Molecular Complexes; Foster, R., Ed.; Elek Science: London, 1974; Vol. 2, Chapter 3.
30. (b) Foster, R. Organic Charge-Transfer Complexes; Academic Press: New York, 1969.
31. Clerk, P.; Simon, S. Table of Spectral Data for Structure Determination of Organic Compounds; Spring-Verlag: Berlin, 1983; P H235.
32. Adrian, F. L. In Chemically Induced Magnetic Polarization; Muus, L. T., Ed.; Reidel. Dordrecht, Holland, 1977; Chapter 5.
33. (a) Roth, H. D. Pure Appl. Chem. 1988, 60, 933.
34. (b) Roth, H. D. Acc. Chem. Res. 1987, 20, 343 and references therein.
35. See for example, (a) Fukuzumi, S.; Kochi, J. A. J. Org. Chem. 1981, 43, 4116. (b) Andrews, L. J.; Keefer, R. M. J. Org. Chem. 1988, 53, 537.
36. See for example, (a) Fukuzumi, S.; Kochi, J. A. J. Org. Chem. 1981, 43, 4116. (b) Andrews, L. J.; Keefer, R. M. J. Org. Chem. 1988, 53, 537.
37. (a) Hubig, S. M.; Beckman, T. M.; Kochi, J. K. J. Am. Chem. Soc. 1997, 119, 2926.
38. (b) Hilinski, E. F.; Milton, S. V.; Rentzepis, P. M. J. Am. Chem. Soc. 1983, 105, 5193.
39. (a) Jones, G., II; Haney, W. A.; Phan, X. T. J. Am. Chem. Soc. 1988, 110, 1922.
40. (b) Jones, G., II.; Mouli, N. J. Phys. Chem. 1988, 92, 717.
41. (c) Jones, G., II.; Mouli, N.; Haney, W. A.; Bergmark, W. R. J. Am. Chem. Soc. 1997, 119, 8788.
42. (a) Kolashi, H.; Funabashi, M.; Kondo, T.; Morita, T.; Ukada, T.; Mataga, N. Bull. Chem. Soc. Jpn. 1984, 57, 3557.
43. (b) Ojima, S.; Mivasaka, H.; Mataga, N. J. Phys. Chem. 1994, 100, 4797.
44. (a) Maslak, P.; Chapman, W. M., Jr. J. Chem. Soc., Chem. Commun. 1989, 1809.
45. (b) Maslak, P.; Chapman, W. H., Jr. J. Org. Chem. 1996, 61, 2647.
46. (a) Bosch, E.; Hubig, S. M.; Kochi, J. K. J. Am. Chem. Soc. 1998, 120, 386.
47. (b) Rathore, R.; Hubig, S. M.; Kochi, J. K. J. Am. Chem. Soc. 1997, 119, 11468.
48. (c) Sun, D.; Hubig, S. M.; Kochi, J. K. J. Am. Org. Chem. 1999, 64, 2250.
49. (d) Hubig, S. M.; Sun, D.; Kochi, J. K. J. Chem. Soc., Perkin Trans. 2 1999, 781.
50. Maruyama, K.; Otsuki, T.; Tai, S. J. Org. Chem. 1985, 50, 52.
51. For reviews, see (a) Gilbert, A. In Synthetic Organic Photochemistry; Horspool, W. M., Ed.; Plenum: New York, 1984. (b) Mccullough, J. J. Chem. Rev. 1987, 87, 811. (c) Cornelisse, J. Chem. Rev. 1993, 93, 615.
52. For reviews, see (a) Gilbert, A. In Synthetic Organic Photochemistry; Horspool, W. M., Ed.; Plenum: New York, 1984. (b) Mccullough, J. J. Chem. Rev. 1987, 87, 811. (c) Cornelisse, J. Chem. Rev. 1993, 93, 615.
53. For reviews, see (a) Gilbert, A. In Synthetic Organic Photochemistry; Horspool, W. M., Ed.; Plenum: New York, 1984. (b) Mccullough, J. J. Chem. Rev. 1987, 87, 811. (c) Cornelisse, J. Chem. Rev. 1993, 93, 615.
54. (a) Bryce-Smith, D.; Gilbert, A.; Orger, B. H.; Tyrrell, H. M. J. Chem. Soc. Chem. Commun. 1974, 334.
55. (b) Gilbert, A. Pure App. Chem. 1980, 52, 2669.
56. (c) Bryth-Smith, D.; Gilbert, A.; Mattay, J. Tetrahedron Lett. 1986, 21, 6011.
57. (a) Mattay, J. Tetrahedron 1986, 41, 2393.
58. (b) Mattay, J. Tetrahedron 1986, 41, 2405.
59. (c) Mattay, J. J. Photochem. 1987, 37, 167.
60. See, for example Wender, P. A.; L. Siggel, Nuss, J. H. [3 + 2] and [5 + 2] Arene-Alkene Photocycloadditions. In Comprehensive Organic Syntheses; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: Elmsford, NY, 1991; Vol. 5, 645-673.
61. (a) Wagner, P. J.; Nahm, K. J. Am. Chem. Soc. 1987, 109, 6528.
62. (b) Wagner, P. J.; Nahm, K. J. Am. Chem. Soc. 1987, 109, 4404.
63. (c) Wagner, P. J.; Cheng, K. L. Tetrahedron Lett. 1993, 34, 907.
64. (d) Wagner, P. J.; Alehashem, H. Tetrahedron Lett. 1993, 34, 914.
65. Cosstick, K. B.; Dew, M. G. B.; Gilbert, A. J. Chem. Soc., Chem. Commun. 1987, 1867.
66. Angus, H. J. F.; Bryce-Smith, D. Proc. Chem. Soc. 1957, 287.
67. Aoyama, H.; Arata, Y.; Omote, Y. J. Chem. Soc., Chem. Commun. 1990, 736.
68. Catalani, L. H.; Toscano, V. G.; de Arruda Campos, I. P. J. Chem. Soc., Perkin Trans. 2, 1995, 1863.
69. Forbes, W. F. Can. J. Chem. 1959, 37, 7.
70. (a) Bryce-Smith, D.; Gilbert, A. Tetrahedron 1976, 32, 1309.
71. (b) Bryce-Smith, D.; Gilbert, A. Tetrahedron 1977, 33, 2459.
72. Houk, K. N. Pure Appl. Chem. 1982, 54, 1633.
73. (a) Fischer, G.; Beckman, E.; Prinzbach, H.; Rihs, G.; Wirz, J. Tetrahedron Lett. 1986, 1273.
74. (b) Sedelmeyer, G.; Fessner, W. D.; Grund, C.; Spurr, P. R.; Fritz, H.; Prinzbach, H. Tetrahedron Lett. 1986, 1277 and references therein.
75. Gleiter, R.; Jahne, G.; Oda, M.; Iyoda, M. J. Org. Chem. 1985, 50, 678.
76. Fischer-Hzalmars, I.; Meza, S. Acta Chem. Scand. 1972, 2991.
77. Matters, S. L.; Farid, S. J. Am. Chem. Soc. 1983, 105, 1386.
78. Kaptain, K. J. Chem. Soc., Chem. Commun. 1971, 732.
79. Roth, H. D.; Schilling, M. L. M. J. Am. Chem. Soc. 1980, 102, 4303.
80. (a) Arnold, D. R.; Du, X. Y.; Chen, J. Can. J. Chem. 1995, 73, 307.
81. (b) Helmstreit, W.; Hanschmann, G. J. Prakt. Chem. 1980, 322, 981.
82. (c) Hanschmann, G.; Helmstreit, W.; Kochler, H. J. Z. Phys. Chem. (Leipzig) 1980, 261, 81.