Photochemical reactions of mercapto/amino substituted alkyl phenylglyoxylates induced by intramolecular electron transfer

Tetrahedron

Volumn 53, Issue 8, 1997, Pages 2751-2766

  Shengkui, Hu ^a   Neckers, Douglas C ^a  

^a BOWLING GREEN STATE UNIVERSITY   (United States)

Author keywords

Amino; Electron transfer; Mercapto; Phenylglyoxylates; Photochemical

Indexed keywords

GLYOXYLIC ACID DERIVATIVE; LACTONE DERIVATIVE;

ARTICLE; ELECTRON TRANSPORT; IN VITRO STUDY; PHOTOCHEMISTRY; PHOTOREACTIVITY; PRIORITY JOURNAL; QUANTUM CHEMISTRY; REACTION ANALYSIS; SPECTROPHOTOMETRY;

EID: 0031584877     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00044-6     Document Type: Article

References (51)

1. 1. Contribution #301 from the Center for Photochemical Sciences.
2. 2. Leermakers, P. A.; Warren, P. C.; Vesley, G. F. J. Am. Chem. Soc. 1964, 86, 1768-1771. Monroe, B. M. Adv. Photochem. Pitts, Jr., J. N.; Hammond, G. S.; Noyes, Jr., W. A. Eds; Wiley-Interscience. 1971, 8, 77-105. Encinas, M. W.; Lissi, E. A.; Zanocco, A.; Stewart, L. C.; Scaiano, J. C. Can J. Chem. 1984, 62, 386-391. Chiang, Y.; Kresge, A.; Pruszynski, P.; Schepp, N. P.; Wirz, J. Angew. Chem. Int. Ed. Engl. 1990, 29, 792-794.
3. 2. Leermakers, P. A.; Warren, P. C.; Vesley, G. F. J. Am. Chem. Soc. 1964, 86, 1768-1771. Monroe, B. M. Adv. Photochem. Pitts, Jr., J. N.; Hammond, G. S.; Noyes, Jr., W. A. Eds; Wiley-Interscience. 1971, 8, 77-105. Encinas, M. W.; Lissi, E. A.; Zanocco, A.; Stewart, L. C.; Scaiano, J. C. Can J. Chem. 1984, 62, 386-391. Chiang, Y.; Kresge, A.; Pruszynski, P.; Schepp, N. P.; Wirz, J. Angew. Chem. Int. Ed. Engl. 1990, 29, 792-794.
4. 2. Leermakers, P. A.; Warren, P. C.; Vesley, G. F. J. Am. Chem. Soc. 1964, 86, 1768-1771. Monroe, B. M. Adv. Photochem. Pitts, Jr., J. N.; Hammond, G. S.; Noyes, Jr., W. A. Eds; Wiley-Interscience. 1971, 8, 77-105. Encinas, M. W.; Lissi, E. A.; Zanocco, A.; Stewart, L. C.; Scaiano, J. C. Can J. Chem. 1984, 62, 386-391. Chiang, Y.; Kresge, A.; Pruszynski, P.; Schepp, N. P.; Wirz, J. Angew. Chem. Int. Ed. Engl. 1990, 29, 792-794.
5. 2. Leermakers, P. A.; Warren, P. C.; Vesley, G. F. J. Am. Chem. Soc. 1964, 86, 1768-1771. Monroe, B. M. Adv. Photochem. Pitts, Jr., J. N.; Hammond, G. S.; Noyes, Jr., W. A. Eds; Wiley-Interscience. 1971, 8, 77-105. Encinas, M. W.; Lissi, E. A.; Zanocco, A.; Stewart, L. C.; Scaiano, J. C. Can J. Chem. 1984, 62, 386-391. Chiang, Y.; Kresge, A.; Pruszynski, P.; Schepp, N. P.; Wirz, J. Angew. Chem. Int. Ed. Engl. 1990, 29, 792-794.
6. 3. Binkley, R. W. J. Org. Chem. 1976, 41, 3030-3031. Carless, H. A. J.; Fekarabobo, G. K. Tetrahedron Lett. 1983, 24, 107-109. Aoyama, H.; Sakamoto, M.; Yoshida, K.; Omote, Y. J. Heterocyclic Chem. 1983, 20, 1099-1101. Tepper, R. J.; Pirrung, M. C. J. Org. Chem. 1995, 60, 2461-2465.
7. 3. Binkley, R. W. J. Org. Chem. 1976, 41, 3030-3031. Carless, H. A. J.; Fekarabobo, G. K. Tetrahedron Lett. 1983, 24, 107-109. Aoyama, H.; Sakamoto, M.; Yoshida, K.; Omote, Y. J. Heterocyclic Chem. 1983, 20, 1099-1101. Tepper, R. J.; Pirrung, M. C. J. Org. Chem. 1995, 60, 2461-2465.
8. 3. Binkley, R. W. J. Org. Chem. 1976, 41, 3030-3031. Carless, H. A. J.; Fekarabobo, G. K. Tetrahedron Lett. 1983, 24, 107-109. Aoyama, H.; Sakamoto, M.; Yoshida, K.; Omote, Y. J. Heterocyclic Chem. 1983, 20, 1099-1101. Tepper, R. J.; Pirrung, M. C. J. Org. Chem. 1995, 60, 2461-2465.
9. 3. Binkley, R. W. J. Org. Chem. 1976, 41, 3030-3031. Carless, H. A. J.; Fekarabobo, G. K. Tetrahedron Lett. 1983, 24, 107-109. Aoyama, H.; Sakamoto, M.; Yoshida, K.; Omote, Y. J. Heterocyclic Chem. 1983, 20, 1099-1101. Tepper, R. J.; Pirrung, M. C. J. Org. Chem. 1995, 60, 2461-2465.
10. 4. Huyser, E. S.; Neckers, D. C. J. Org. Chem. 1964, 29, 276-278.
11. 5. Hu, S.; Neckers, D. C. J. Org. Chem. 1996, 61, 6407-6415.
12. 6. Hu, S.; Neckers, D. C. J. Org. Chem. in press.
13. 7. Wagner, P. J.; Lindstrom, M. J. J. Am. Chem. Soc. 1987, 109, 3057-3062.
14. 13CNMR were obtained. However, they were not stable enough for MS analysis as we have reported in reference 2. Those α-alkoxyl acetaldehydes were observed by NMR when the reactions were carried out in NMR tubes. They were not isolated since their existence has been well documented (ref. 2 and references therein).
15. 9. For a similar observation in sulfide-containing phthalimides, see Sato, Y.; Nakai, H.; Mizoguchi, T.; Hatanaka, Y.; Kanaoka, Y. J. Am. Chem. Soc. 1976, 98, 2349-2351.
16. 10. Guttenplan, J. B., Cohen, S. G. J. Org. Chem. 1973, 38, 2001-2007. Cohen, S. G.; Ojanpera, S. J. Am. Chem. Soc. 1975, 97, 5633-5634.
17. 10. Guttenplan, J. B., Cohen, S. G. J. Org. Chem. 1973, 38, 2001-2007. Cohen, S. G.; Ojanpera, S. J. Am. Chem. Soc. 1975, 97, 5633-5634.
18. 11. Kachevar, I.; Wagner, P. J. J. Am. Chem. Soc. 1972, 94, 3859-3865. Cohen, S. G.; Parola, A.; Parsons, Jr., G. H. Chem. Rev. 1973, 73, 141-161.
19. 11. Kachevar, I.; Wagner, P. J. J. Am. Chem. Soc. 1972, 94, 3859-3865. Cohen, S. G.; Parola, A.; Parsons, Jr., G. H. Chem. Rev. 1973, 73, 141-161.
20. 12. Dalton, J. C.; Turro, N. J. J. Am. Chem. Soc. 1971, 93, 3569-3570.
21. 13. Winnik, M. A. Chem. Rev. 1981, 81, 491-524. Wagner, P. J. Acc. Chem. Res. 1983, 16, 461-467.
22. 13. Winnik, M. A. Chem. Rev. 1981, 81, 491-524. Wagner, P. J. Acc. Chem. Res. 1983, 16, 461-467.
23. 14. Turro, N. J.; Dalton, J. C.; Farrington, G.; Niemczyk, M.; Pond, D. M. J. Am. Chem. Soc. 1970, 92, 6978-6979. Caldwell, R. A.; Creed, D. Acc. Chem. Res. 1980, 13, 45-50.
24. 14. Turro, N. J.; Dalton, J. C.; Farrington, G.; Niemczyk, M.; Pond, D. M. J. Am. Chem. Soc. 1970, 92, 6978-6979. Caldwell, R. A.; Creed, D. Acc. Chem. Res. 1980, 13, 45-50.
25. 15. Wagner, P. J.; Giri, B. P.; Frerking, Jr., H. W.; DeFrancesco, J. J. Am. Chem. Soc. 1992, 114, 8326-8327. Wagner, P. J.; Frerking, Jr., H. W. Can. J. Chem. 1995, 73, 2047-2061.
26. 15. Wagner, P. J.; Giri, B. P.; Frerking, Jr., H. W.; DeFrancesco, J. J. Am. Chem. Soc. 1992, 114, 8326-8327. Wagner, P. J.; Frerking, Jr., H. W. Can. J. Chem. 1995, 73, 2047-2061.
27. 16. For similar observation, see Hoshino, M.; Koizumi, M. Chem. Letters, 1972, 189-191.
28. 17. Turro, N. J. "Modern Molecular Photochemistry," University Science Books, 1991, 374.
29. 18. (a) Wagner, P. J.; Jellinek, T.; Kemppainen, A. E. J. Am. Chem. Soc. 1972, 94, 7512-7519. Wagner, P. J.; Ersfeld, D. A. J. Am. Chem. Soc. 1976, 98, 4515-4518. Wagner, P. J.; Ersfeld D. A.; Scheve, B. J. In The Exciplex, Gordon, M.; Ware, W. R. Eds; Academic Press; New York, 1975, pp 359-372.
30. 18. (a) Wagner, P. J.; Jellinek, T.; Kemppainen, A. E. J. Am. Chem. Soc. 1972, 94, 7512-7519. Wagner, P. J.; Ersfeld, D. A. J. Am. Chem. Soc. 1976, 98, 4515-4518. Wagner, P. J.; Ersfeld D. A.; Scheve, B. J. In The Exciplex, Gordon, M.; Ware, W. R. Eds; Academic Press; New York, 1975, pp 359-372.
31. 18. (a) Wagner, P. J.; Jellinek, T.; Kemppainen, A. E. J. Am. Chem. Soc. 1972, 94, 7512-7519. Wagner, P. J.; Ersfeld, D. A. J. Am. Chem. Soc. 1976, 98, 4515-4518. Wagner, P. J.; Ersfeld D. A.; Scheve, B. J. In The Exciplex, Gordon, M.; Ware, W. R. Eds; Academic Press; New York, 1975, pp 359-372.
32. (b) Wagner, P. J.; Lindstrom, M. J. J. Am. Chem. Soc. 1987, 109, 3062-3067.
33. 19. Aoyama, H.; Hasegawa, T.; Watabe, M.; Shiraishi, H.; Omote, Y. J. Org. Chem. 1978, 43, 419-422 . Aoyama, H.; Sakamoto, M.; Kuwabara, K.; Yoshida, K.; Omote, Y. J. Am. Chem. Soc. 1983, 105, 1958-1964 . Griesbeck, A. G.; Mauder, H. Angew. Chem. Int. Ed. Engl. 1992, 31, 73-75. Azzouzi, A.; Dufour, M.; Gramain, J.-C.; Remuson, R. Heterocycles, 1988, 27, 133-148 . Wessig, P.; Wettstein, P.; Giese, B.; Neuburger, M.; Zehnder, M. Helv. Chim. Acta. 1994, 77, 829-837. Hashizume, D.; Kogo, H.; Sekine, A.; Ohashi, Y.; Miyamoto, H.; Toda, F. J. Chem. Soc., Perkin Trans. 2 1996, 61-66.
34. 19. Aoyama, H.; Hasegawa, T.; Watabe, M.; Shiraishi, H.; Omote, Y. J. Org. Chem. 1978, 43, 419-422 . Aoyama, H.; Sakamoto, M.; Kuwabara, K.; Yoshida, K.; Omote, Y. J. Am. Chem. Soc. 1983, 105, 1958-1964 . Griesbeck, A. G.; Mauder, H. Angew. Chem. Int. Ed. Engl. 1992, 31, 73-75. Azzouzi, A.; Dufour, M.; Gramain, J.-C.; Remuson, R. Heterocycles, 1988, 27, 133-148 . Wessig, P.; Wettstein, P.; Giese, B.; Neuburger, M.; Zehnder, M. Helv. Chim. Acta. 1994, 77, 829-837. Hashizume, D.; Kogo, H.; Sekine, A.; Ohashi, Y.; Miyamoto, H.; Toda, F. J. Chem. Soc., Perkin Trans. 2 1996, 61-66.
35. 19. Aoyama, H.; Hasegawa, T.; Watabe, M.; Shiraishi, H.; Omote, Y. J. Org. Chem. 1978, 43, 419-422 . Aoyama, H.; Sakamoto, M.; Kuwabara, K.; Yoshida, K.; Omote, Y. J. Am. Chem. Soc. 1983, 105, 1958-1964 . Griesbeck, A. G.; Mauder, H. Angew. Chem. Int. Ed. Engl. 1992, 31, 73-75. Azzouzi, A.; Dufour, M.; Gramain, J.-C.; Remuson, R. Heterocycles, 1988, 27, 133-148 . Wessig, P.; Wettstein, P.; Giese, B.; Neuburger, M.; Zehnder, M. Helv. Chim. Acta. 1994, 77, 829-837. Hashizume, D.; Kogo, H.; Sekine, A.; Ohashi, Y.; Miyamoto, H.; Toda, F. J. Chem. Soc., Perkin Trans. 2 1996, 61-66.
36. 19. Aoyama, H.; Hasegawa, T.; Watabe, M.; Shiraishi, H.; Omote, Y. J. Org. Chem. 1978, 43, 419-422 . Aoyama, H.; Sakamoto, M.; Kuwabara, K.; Yoshida, K.; Omote, Y. J. Am. Chem. Soc. 1983, 105, 1958-1964 . Griesbeck, A. G.; Mauder, H. Angew. Chem. Int. Ed. Engl. 1992, 31, 73-75. Azzouzi, A.; Dufour, M.; Gramain, J.-C.; Remuson, R. Heterocycles, 1988, 27, 133-148 . Wessig, P.; Wettstein, P.; Giese, B.; Neuburger, M.; Zehnder, M. Helv. Chim. Acta. 1994, 77, 829-837. Hashizume, D.; Kogo, H.; Sekine, A.; Ohashi, Y.; Miyamoto, H.; Toda, F. J. Chem. Soc., Perkin Trans. 2 1996, 61-66.
37. 19. Aoyama, H.; Hasegawa, T.; Watabe, M.; Shiraishi, H.; Omote, Y. J. Org. Chem. 1978, 43, 419-422 . Aoyama, H.; Sakamoto, M.; Kuwabara, K.; Yoshida, K.; Omote, Y. J. Am. Chem. Soc. 1983, 105, 1958-1964 . Griesbeck, A. G.; Mauder, H. Angew. Chem. Int. Ed. Engl. 1992, 31, 73-75. Azzouzi, A.; Dufour, M.; Gramain, J.-C.; Remuson, R. Heterocycles, 1988, 27, 133-148 . Wessig, P.; Wettstein, P.; Giese, B.; Neuburger, M.; Zehnder, M. Helv. Chim. Acta. 1994, 77, 829-837. Hashizume, D.; Kogo, H.; Sekine, A.; Ohashi, Y.; Miyamoto, H.; Toda, F. J. Chem. Soc., Perkin Trans. 2 1996, 61-66.
38. 19. Aoyama, H.; Hasegawa, T.; Watabe, M.; Shiraishi, H.; Omote, Y. J. Org. Chem. 1978, 43, 419-422 . Aoyama, H.; Sakamoto, M.; Kuwabara, K.; Yoshida, K.; Omote, Y. J. Am. Chem. Soc. 1983, 105, 1958-1964 . Griesbeck, A. G.; Mauder, H. Angew. Chem. Int. Ed. Engl. 1992, 31, 73-75. Azzouzi, A.; Dufour, M.; Gramain, J.-C.; Remuson, R. Heterocycles, 1988, 27, 133-148 . Wessig, P.; Wettstein, P.; Giese, B.; Neuburger, M.; Zehnder, M. Helv. Chim. Acta. 1994, 77, 829-837. Hashizume, D.; Kogo, H.; Sekine, A.; Ohashi, Y.; Miyamoto, H.; Toda, F. J. Chem. Soc., Perkin Trans. 2 1996, 61-66.
39. 20. The difference in electron richness of the sulfur and the amide nitrogen may also due to their different degrees of conjugation with the carbonyl group. We thank the referees for bringing this to our attention.
40. 21. For a theoretical discussion, see Guttenplan, J. B.; Cohen, S. G. J. Am. Chem. Soc. 1972, 94, 4040-4042. Salem, L. J. Am. Chem. Soc. 1974, 96, 3486-3501.
41. 21. For a theoretical discussion, see Guttenplan, J. B.; Cohen, S. G. J. Am. Chem. Soc. 1972, 94, 4040-4042. Salem, L. J. Am. Chem. Soc. 1974, 96, 3486-3501.
42. 22. Arroyo, P.; Norte, M.; Vázquez, J. T.; Nakanishi, K. J. Org. Chem. 1991, 56, 2671-2675. Mehta, G.; Krishnamurthy, N.; Karra, S. R. J. Am. Chem. Soc. 1991, 113, 5765-5775. Heathcock, C. H.; Graham, S. L.; Pirrung, M. C.; Plavac, F.; White, C. T. In The Total Synthesis of Natural Products; ApSimon, J.; Ed.; John Wiley & Sons; New York, 1983, Vol. 5, 333-383. Snider, B. B.; Yang, K. J. Org. Chem. 1990, 55, 4392-4399. Weenen, H.; Nkunya, M. H. H.; Magani, Q. A.; Posthumus, M. A.; Waibel, R.; Achenbach, H. J. Org. Chem. 1991, 56, 5865-5867.
43. 22. Arroyo, P.; Norte, M.; Vázquez, J. T.; Nakanishi, K. J. Org. Chem. 1991, 56, 2671-2675. Mehta, G.; Krishnamurthy, N.; Karra, S. R. J. Am. Chem. Soc. 1991, 113, 5765-5775. Heathcock, C. H.; Graham, S. L.; Pirrung, M. C.; Plavac, F.; White, C. T. In The Total Synthesis of Natural Products; ApSimon, J.; Ed.; John Wiley & Sons; New York, 1983, Vol. 5, 333-383. Snider, B. B.; Yang, K. J. Org. Chem. 1990, 55, 4392-4399. Weenen, H.; Nkunya, M. H. H.; Magani, Q. A.; Posthumus, M. A.; Waibel, R.; Achenbach, H. J. Org. Chem. 1991, 56, 5865-5867.
44. 22. Arroyo, P.; Norte, M.; Vázquez, J. T.; Nakanishi, K. J. Org. Chem. 1991, 56, 2671-2675. Mehta, G.; Krishnamurthy, N.; Karra, S. R. J. Am. Chem. Soc. 1991, 113, 5765-5775. Heathcock, C. H.; Graham, S. L.; Pirrung, M. C.; Plavac, F.; White, C. T. In The Total Synthesis of Natural Products; ApSimon, J.; Ed.; John Wiley & Sons; New York, 1983, Vol. 5, 333-383. Snider, B. B.; Yang, K. J. Org. Chem. 1990, 55, 4392-4399. Weenen, H.; Nkunya, M. H. H.; Magani, Q. A.; Posthumus, M. A.; Waibel, R.; Achenbach, H. J. Org. Chem. 1991, 56, 5865-5867.
45. 22. Arroyo, P.; Norte, M.; Vázquez, J. T.; Nakanishi, K. J. Org. Chem. 1991, 56, 2671-2675. Mehta, G.; Krishnamurthy, N.; Karra, S. R. J. Am. Chem. Soc. 1991, 113, 5765-5775. Heathcock, C. H.; Graham, S. L.; Pirrung, M. C.; Plavac, F.; White, C. T. In The Total Synthesis of Natural Products; ApSimon, J.; Ed.; John Wiley & Sons; New York, 1983, Vol. 5, 333-383. Snider, B. B.; Yang, K. J. Org. Chem. 1990, 55, 4392-4399. Weenen, H.; Nkunya, M. H. H.; Magani, Q. A.; Posthumus, M. A.; Waibel, R.; Achenbach, H. J. Org. Chem. 1991, 56, 5865-5867.
46. 22. Arroyo, P.; Norte, M.; Vázquez, J. T.; Nakanishi, K. J. Org. Chem. 1991, 56, 2671-2675. Mehta, G.; Krishnamurthy, N.; Karra, S. R. J. Am. Chem. Soc. 1991, 113, 5765-5775. Heathcock, C. H.; Graham, S. L.; Pirrung, M. C.; Plavac, F.; White, C. T. In The Total Synthesis of Natural Products; ApSimon, J.; Ed.; John Wiley & Sons; New York, 1983, Vol. 5, 333-383. Snider, B. B.; Yang, K. J. Org. Chem. 1990, 55, 4392-4399. Weenen, H.; Nkunya, M. H. H.; Magani, Q. A.; Posthumus, M. A.; Waibel, R.; Achenbach, H. J. Org. Chem. 1991, 56, 5865-5867.
47. 23. see for example: Curran, D. P. Synthesis 1988, 417-439, 489-513. Ramaiah, M. Tetrahedron 1987, 43, 3541-3676. Giese, B. Radicals in Organic Synthesis: Formation of Carbon-carbon Bonds; Pergamon: Oxford, 1986.
48. 23. see for example: Curran, D. P. Synthesis 1988, 417-439, 489-513. Ramaiah, M. Tetrahedron 1987, 43, 3541-3676. Giese, B. Radicals in Organic Synthesis: Formation of Carbon-carbon Bonds; Pergamon: Oxford, 1986.
49. 23. see for example: Curran, D. P. Synthesis 1988, 417-439, 489-513. Ramaiah, M. Tetrahedron 1987, 43, 3541-3676. Giese, B. Radicals in Organic Synthesis: Formation of Carbon-carbon Bonds; Pergamon: Oxford, 1986.
50. 24. Lewis, F. D.; Hilliard, T. A. J. Am. Chem. Soc. 1972,94, 3852-3857.
51. 25. Ford, W. E.; Rodgers, M. A. J. J. Phys. Chem. 1994, 98, 3822-3831.