Chemoselective photorearrangements of diazinobarrelenes. Deuterium labeling study

Journal of Organic Chemistry

Volumn 72, Issue 25, 2007, Pages 9690-9697

  Chen, Ann Cheng ^a   Chuang, Gary J ^a   Villarante, Nelson R ^a,b   Liao, Chun Chen ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

^b UNIVERSITY OF THE PHILIPPINES MANILA   (Philippines)

Author keywords

[No Author keywords available]

Indexed keywords

DIAZINOBARRELENES; PHOTOCHEMICAL BEHAVIOR; PHOTOREARRANGEMENTS;

CHEMICAL STABILITY; IRRADIATION; PHOTOLYSIS;

DEUTERIUM;

BARRELENE DERIVATIVE; BENZOQUINONE DERIVATIVE; DEUTERIUM; ORGANIC COMPOUND; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRAZINE DERIVATIVE; QUINOXALINE DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CHEMICAL LABELING; CHEMICAL REACTION; CHEMOSENSITIVITY; ENERGY; IRRADIATION; MOLECULAR STABILITY; PHOTOCHEMISTRY; QUALITATIVE ANALYSIS;

EID: 36849026025     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo7016795     Document Type: Article

References (79)

1. (a) Zimmerman, H. E.; Paufler, R. M. J. Am. Chem. Soc. 1960, 82, 1514.
2. (b) Hassenruck, K.; Martin, H.-D. Chem. Rev. 1989, 89, 1125.
3. (c) Gedanken, A.; de Meijere, A. J. Chem. Phys. 1988, 88, 4153.
4. (d) Yamamoto, S.; Nakata, M.; Fukuyama, T.; Kuchitsu, K.; Hasselmann, D.; Ermer, O. J. Phys. Chem. 1982, 86, 529.
5. (e) Zimmerman, H. E.; Boettcher, R. J.; Buehler, N. E.; Keck, G. E. J. Am. Chem. Soc. 1975, 97, 5635.
6. (f) Hoffman, R.; Heilbrunner, E.; Gleiter, R. J. Am. Chem. Soc. 1970, 92, 706.
7. Zimmerman, H. E.; Grunewald, G. L. J. Am. Chem. Soc. 1966, 88, 183.
8. (a) Ramaiah, D.; Sajimon, M. C.; Joseph, J.; George, M. V. Chem. Soc. Rev. 2005, 34, 48.
9. (b) Liao, C.-C.; Peddinti, R. K. In CRC Handbook of Organic Photochemistry and Photobiology, 2nd ed.; Horspool, W. M., Lenci, F., Eds.; CRC Press: Boca Raton, FL, 2004; p 32/1.
10. (c) Altundas, R.; Dastan, A.; Unaldi, N. S.; Güven, K.; Uzun, O.; Balci, M. Eur. J. Org. Chem. 2002, 3, 526.
11. (d) Sajimon, M. C.; Ramaiah, D.; Kumar, S. A.; Rath, N. P.; George, M. V. Tetrahedron 2000, 56, 5421.
12. (e) Chen, J.; Pokkuluri, P. R.; Scheffer, J. R.; Trotter, J. Acta Crystallogr. 1993, B49, 905.
13. (f) Liao, C.-C.; Lin, S.-Y.; Hsieh, H.-P.; Yang, P.-H. J. Chin. Chem. Soc. 1992, 39, 275.
14. (g) Liao, C.-C.; Yang, P.-H. J. Chem. Soc., Chem. Commun. 1991, 626.
15. (h) Liao, C.-C.; Hsieh, H.-P.; Lin, S.-Y. J. Chem Soc., Chem. Commun. 1990, 545.
16. (a) Dura, R. D.; Paquette, L. A. J. Org. Chem. 2006, 71, 2456.
17. (b) McClure, C. K.; Kiessling, A. J.; Link, J. S. Org. Lett. 2003, 5, 3811.
18. (c) Janssen, R. A. J.; Hummelen, J. C.; Wudl, F. J. Am. Chem. Soc. 1995, 117, 544.
19. (d) Givens, R. S.; Oettle, W. F. J. Am. Chem. Soc. 1971, 93, 3963.
20. (e) Prinzbach, H. Pure Appl. Chem. 1968, 16, 17.
21. (f) Ciganek, E. J. Am. Chem. Soc. 1966, 88, 2882.
22. (a) Zimmerman, H. E.; Cirkva, V. Org. Lett. 2000, 2, 2365.
23. (b) Zimmerman, H. E.; Armesto, D. Chem. Rev. 1996, 96, 3065.
24. (c) Armesto, D. In Handbook of Photochemistry and Photobiology; Horspool, W. M., Song, P.-S., Eds.; CRC Press: Boca Raton, FL, 1995; Chapter 73.
25. (d) Zimmerman, H. E. Org. Photochem. 1991, 11, 1.
26. (e) Zimmerman, H. E. In Rearrangements in Ground and Excited States; de Mayo, P., Ed.; Academic Press: New York, 1980; Vol. 3, p 131.
27. (f) Hixson, S. S.; Mariano, P. S.; Zimmerman, H. E. Chem. Rev. 1973, 73, 531.
28. (a) Zimmerman, H. E.; Binkley, R. W.; Givens, R. S.; Grunewald, G. L.; Sherwin, M. A. J. Am. Chem. Soc. 1969, 91, 3316.
29. (b) Zimmerman, H. E.; Binkley, R. W.; Givens, R. S.; Sherwin, M. A. J. Am. Chem. Soc. 1967, 89, 3932.
30. Zimmerman, H. E.; Boettcher, R. J.; Buehler, N. E.; Keck, G. E.; Steinmetz, M. G. J. Am. Chem. Soc. 1976, 98, 7680.
31. (a) Frutos, L. M.; Sancho, U.; Castaño, O. Org. Lett. 2004, 6, 1229.
32. (b) Zimmerman, H. E.; Kutateladze, A. G.; Maekawa, Y.; Mangette, F. J. Am. Chem. Soc. 1994, 116, 9795.
33. (c) Zimmerman, H. E.; Sulzbach, H. M.; Tollefson, M. B. J. Am. Chem. Soc. 1993, 115, 6548.
34. (a) Armesto, D.; Caballero, O.; Ortiz, M. J.; Agarrabeitia, A. R.; Martin-Fontecha, M.; Torres, M. R. J. Org. Chem. 2003, 68, 6661.
35. (b) Armesto, D.; Gallego, M. G.; Horspool, W. M.; Agarrabeitia, A. R. Tetrahedron 1995, 51, 9223.
36. (c) Armesto, D.; Ortiz, M. J.; Ramos, A.; Horspool, W. M.; Mayoral, E. P. J. Org. Chem. 1994, 59, 8115.
37. (a) Singh, V. In CRC Handbook of Organic Photochemistry and Photobiology, 2nd ed.; Horspool, W. M., Lenci, F., Eds.; CRC Press: Boca Raton, FL, 2004; p 78/1.
38. (b) Liao, C.-C. In CRC Handbook of Organic Photochemistry and Photobiology; Horspool, W. M., Soon, P. S., Eds.; CRC Press: Boca Raton, FL, 1995; p 194.
39. (c) Demuth, M. Org. Photochem. 1991, 11, 37.
40. (a) Zimmerman, H. E.; Givens, R. S.; Pagni, R. M.; J. Am. Chem. Soc. 1968, 90, 6096.
41. (b) Zimmerman, H. E.; Givens, R. S.; Pagni, R. M. J. Am. Chem. Soc. 1968, 90, 4191.
42. Zimmerman, H. E.; Bender, C. O. J. Am. Chem. Soc. 1970, 92, 4366.
43. Zimmerman, H. E.; Amick, D. R. J. Am. Chem. Soc. 1973, 95, 3977.
44. (a) Chittimalla, S. K.; Shiao, H.-Y.; Liao, C.-C. Org. Biomol. Chem. 2006, 4, 2267.
45. (b) Liao, C.-C.; Peddinti, R. K. Acc. Chem. Res. 2002, 35, 856.
46. (c) Gao, S.-Y. Ph.D. Thesis, Department of Chemistry, National Tsing-Hua University, Taiwan, 2005.
47. (a) Scharf, H.-D.; Klar, R. Chem. Ber. 1972, 105, 575.
48. (b) Scharf, H.-D.; Klar, R. Tetrahedron Lett. 1971, 12, 517.
49. (c) McMahon, R. J.; Abelt, C. J.; Chapman, O. L.; Johnson, J. W. Kreil, C. L.; LeRoux, J.-P.; Mooring, A. M.; Wede, P. R. J. Am. Chem. Soc. 1987, 109, 2456.
50. (a) Bender, C. O.; Dolman, D.; Foesier, J. C.; Lawson, S. L.; Preuss, K. E. Can. J. Chem. 2003, 81, 37.
51. (b) Bender, C. O.; Bengton, D. L.; Dolman, D.; Herle, C. E. L.; O'Shea, S. F. Can. J. Chem. 1982, 60, 1942.
52. (c) Luibrand, R. T.; Broline, B. M.; Charles, K. A.; Drues, R. W. J. Org. Chem. 1981, 46, 1874.
53. (d) Luibrand, R. T.; Fujinari, E. M. J. Org. Chem. 1980, 45, 958.
54. (e) Zimmerman, H. E.; Viriot-Villaume, M.-L. J. Am. Chem. Soc. 1973, 95, 1274.
55. (a) Malkin, Y. N.; Kuz'min, V. A. Russ. Chem. Rev. 1990, 59, 279.
56. (b) Leinwand, D. A.; Lefkowitz, S. M.; Brenner, H. C. J. Am. Chem. Soc. 1985, 107, 6179.
57. (c) Yamazaki, I.; Murao, T.; Yamanaka, T.; Yoshihara, K. Faraday Discuss. Chem. Soc. 1983, 75, 395.
58. (d) Scott, G. W.; Boldridge, D. W.; Spiglanin, T. A. J. Phys. Chem. 1982, 86, 1976.
59. (e) Madej, S. L.; Gillispie, G. D.; Lim, E. C. Chem. Phys. 1978, 32, 1.
60. (f) Bent, D. V.; Hayon, E. P.; Moorfhy, N. J. Am. Chem. Soc. 1975, 97, 5065.
61. (a) Pan, Y.; Sheng, Z.; Ye, X.; Ao, Z.; Chu, G.; Dai, J.; Yu, S. J. Photochem. Photobiol. A: Chem. 2005, 174, 98.
62. (b) Shim, S. C.; Kim, M. S.; Lee, K. T.; Jeong, B. M.; Lee, B. H. J. Photochem. Photobiol. A: Chem. 1992, 65, 121.
63. (c) Bartocci, G.; Massetti, F.; Mazzucato, U.; Marconi, G. J. Chem. Soc., Faraday Trans. 2 1984, 80, 1093.
64. (d) Yajima, Y.; Lim, E. C. Chem. Phys. Lett. 1980, 73, 249.
65. (e) Fischer, G. Chem. Phys. Lett. 1975, 33, 459.
66. (a) Kopecky, J. Organic Photochemistry: A Visual Approach; VCH: Cambridge, U.K., 1992.
67. (b) Turro, N. J. Modern Molecular Photochemistry; University Science Books: Sausalito, CA, 1991.
68. (a) Zipse, H. Top. Curr. Chem. 2006, 263, 163.
69. (b) Sajimon, M. C.; Ramaiah, D.; Muneer, M.; Ajithkumar, E. S.; Rath, N. P.; George, M. V. J. Org. Chem. 1999, 64, 6347.
70. (c) Yeh-Ku, A.; Paquette, L. A.; Rozeboom, M. D.; Houk, K. N. J. Am. Chem. Soc. 1979, 101, 5981.
71. (d) Paquette, L. A.; Cottrell, D. M.; Snow, R. A.; Gifkins, K. B.; Clardy, J. J. Am. Chem. Soc. 1975, 97, 3275.
72. (a) Zimmerman, H. E.; Novak, T. J. Org. Chem. 2003, 68, 5056.
73. (b) Ito, Y.; Nishimura, H.; Umehara, Y.; Yamada, Y.; Tone, M.; Matsuura, T. J. Am. Chem. Soc. 1983, 105, 1590.
74. (c) Arnold, D. R.; Bolton, J. R.; Palmer, G. E.; Prabhu, K. V. Can. J. Chem. 1977, 55, 2728.
75. (a) Loutfy, R. O. Can. J. Chem. 1976, 54, 1454.
76. (b) Murov, S. L. Handbook of Photochemistry; Marcel Dekker: New York, 1973; p 3.
77. (c) Crowley, K. J. Proc. Chem. Soc. 1962, 245.
78. (d) Evans, D. F. J. Chem. Soc. 1960, 1735.
79. (e) Evans, D. F. J. Chem. Soc. 1957, 1351.