The Photochemistry of Polydonor-Substituted Phthalimides: Curtin-Hammett-Type Control of Competing Reactions of Potentially Interconverting Zwitterionic Biradical Intermediates

Journal of the American Chemical Society

Volumn 126, Issue 4, 2004, Pages 1110-1124

  Yoon, Ung Chan ^a   Kwon, Hyuk Chul ^a   Hyung, Tae Gyung ^a   Choi, Kyung Hwa ^a   Oh, Sun Wha ^a   Yang, Shaorong ^b   Zhao, Zhiming ^b   Mariano, Patrick S ^b  

^a Pusan National University   (South Korea)

^b UNIVERSITY OF NEW MEXICO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ETHERS; FLUORESCENCE; FREE RADICALS; OXIDATION; PHOTOCHEMICAL REACTIONS; QUANTUM THEORY; STEREOCHEMISTRY; SUBSTRATES;

OXIDATION POTENTIALS;

AROMATIC COMPOUNDS;

ALPHA CARBOXYMETHANESULFONAMIDE; ALPHA TRIMETHYLSILYLMETHANESULFONAMIDE; AMINE; AMPHOLYTE; CATION; ETHER; FUNCTIONAL GROUP; IMIDE; MESYLIC ACID DERIVATIVE; NAPHTHALENE DERIVATIVE; NAPHTHALIMIDE DERIVATIVE; PHTHALIMIDE DERIVATIVE; RADICAL; SULFIDE; SULFONAMIDE; TRIMETHYLSILYL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CYCLIZATION; DECARBOXYLATION; DEPROTONATION; DESILYLATION; ELECTRON TRANSPORT; ENERGY; FLUORESCENCE; FRAGMENTATION REACTION; OXIDATION REDUCTION POTENTIAL; PHOTOCHEMISTRY; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0942298046     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0305712     Document Type: Article

References (36)

1. Ohga, K.; Mariano. P. S. J. Am. Chem. Soc. 1982, 104, 617.
2. Ohga, K.; Yoon, U. C.; Mariano, P. S. J. Og. Chem. 1984, 49, 213.
3. Borg, R. M.; Heuckeroth, R. O.; Lan, A. J. Y.; Quillen, S. L.; Mariano, P. S. J. Am. Chem. Soc. 1987, 109, 2728.
4. Lan, A. J. Y.; Heuckeroth, R. O.; Mariano, P. S. J. Am. Chem. Soc. 1987, 109, 2738.
5. Kavash, R. W.; Mariano, P. S. Tetrahedron Lett. 1989, 31, 4185.
6. Ho, G. D.; Mariano, P. S. J. Org. Chem. 1988, 53, 5113.
7. Ahmed-Schofield, R.; Mariano, P. S. J. Org. Chem. 1987, 52, 1478.
8. Hasegawa, E.; Xu, W.; Mariano, P. S.; Yoon, U. C.; Kim, J. U. J. Am. Chem. Soc. 1988, 109, 8089.
9. Xu, W.; Zhang, X. M.; Mariano, P. S J. Am. Chem. Soc. 1991, 113, 8847.
10. Jeon, Y. T.; Lee, C. P.; Mariano, P. S. J. Am. Chem. Soc. 1991, 113, 8863.
11. Yoon, U. C.; Mariano, P. S. Acc. Chem. Res. 1992, 25, 233.
12. Jung, Y. S.; Swartz, W. S.; Swanz, W. H.; Xu, W.; Mariano, P. S.; Green, N. J.; Schultz, A. G. J. Org. Chem. 1992, 57, 6037.
13. Khim, S. K.; Mariano, P. S. Tetrahedron Lett. 1993, 35, 999.
14. Zhang, X. M.; Yeh, S. R.; Hong, S.; Freccero, M.; Albini, A.; Falvey, D. E.; Mariano, P. S. J. Am. Chem. Soc. 1994, 116, 4211.
15. Su Z.; Falvey, D. E.; Yoon, U. C.; Mariano, P. S. J. Am. Chem. Soc. 1997, 119, 5261.
16. Su Z.; Falvey, D. E.; Yoon, U. C.; Oh, S. W.; Mariano, P. S. J. Am. Chem. Soc. 1997, 120, 10676.
17. Yoon, U. C.; Kim, J. W.; Ryu, J. Y.; Cho, S. J.; Oh, S. W.; Mariano, P. S. J. Photochem. Photobiol. A 1997, 106, 145.
18. Yoon, U. C.; Oh, S. W.; Lee, J. H.; Park, J. H.; Kang, K. T.; Mariano, P. S. J. Org. Chem. 2001, 66, 939.
19. Yoon, U. C.; Jin. Y. X.; Oh, S. W.; Park, C. H.; Park, J. H.; Campana, C. F.; Cai, X.; Duesler, E. N.; Mariano, P. S. J. Am. Chem. Soc. 2003, 125, 10664.
20. Lewis, F. D.; Liu, X.; Liu, J.; Miller, S. E.; Hayes, R. T.; Wasielewski, M. R. Nature 2000, 406, 51.
21. Sartor, V.; Boone, E.; Schuster. G. B. J. Phys. Chem. B 2001, 105, 11057.
22. Giese, B. Curr. Opin. Chem. Biol. 2001, 6, 612.
23. Curtin, D. Y. Stereochemical Control of Organic Reactions. Record Chem. Progr. (Kresge-Hooker Sci. Lib.) 1954, 15, 111.
24. Mitsunobo, O. Synthesis 1981, 1.
25. Valat, P.; Wintgens, V.; Kossanyi, J.; Biczok, L.; Demeter, A.; Berces, T. J. Am. Chem. Soc. 1992, 114, 946.
26. Wintgens, V.; Valat, P.; Kossanyi, J.; Biczok, L.; Demeter, A.; Berces, T. J. Chem. Soc. Faraday Trans. 1994, 90, 411.
27. Demeter, A.; Berces; Biczok, L.; Wintgens, V.; Valat, P.; Kossanyi, J. J. Chem. Soc. Faraday Trans. 1994, 90, 2635.
28. Oxidation potentials of tertiary amines are significantly lower than that of carboxylates. Thus, SET from the carboxylate to the excited naphthalimide chromophore is not likely. Confirmation of this proposal is found in LFP studies (ref 16) of α-aminocarboxylate-derived cation radicals.
29. See: Oevering, H.; Paddon-Row, M. N.; Heppener, M.; Oliver, A. M.; Cotsaris, E.; Verhoeven, J. W.; Hush, N. S. J. Am. Chem. Soc. 1987, 109, 3258, Yonemoto, E. H.; Saupe, G. B.; Schnehl, R. H.; Hubig, S. M.; Riley, R. L.; Iverson, B. L.; Mallouk, T. E. J. Am. Chem. Soc. 1994, 116, 4786 and references therein.
30. See: Oevering, H.; Paddon-Row, M. N.; Heppener, M.; Oliver, A. M.; Cotsaris, E.; Verhoeven, J. W.; Hush, N. S. J. Am. Chem. Soc. 1987, 109, 3258, Yonemoto, E. H.; Saupe, G. B.; Schnehl, R. H.; Hubig, S. M.; Riley, R. L.; Iverson, B. L.; Mallouk, T. E. J. Am. Chem. Soc. 1994, 116, 4786 and references therein.
31. Somich, C.; Mazzocchi, P. H.; Edwards, M.; Morgan, T.; Ammon, H. L. J. Org. Chem. 1990, 55, 2624.
32. Shono, T.; Matsumura, Y.; Tsubata, K.; Uchida, K.; Kanazawa, T.; Tsuda, K. J. Org. Chem. 1984, 49, 3711.
33. Estimated on the basis of oxidation potentials of alcohols given in Lund, H. Acta Chem. Scand. 1957, 11, 491.
34. Cottrell. P. T.; Mann, C. K. J. Electrochem. Soc. 1969, 116, 1499.
35. Mann, C. K. Anal. Chem. 1964, 36, 2424.
36. This is analogous to the Winstein-Holness treatment of the dependence of reaction rates on the population and reactivity of rapidly equilibrating species found in Winstein, S.; Holness, N. J. J. Am. Chem. Soc. 1955, 77, 5562.