Mechanism one-electron oxidation of β-, γ-, and δ-hydroxyalkyl sulfides. Catalysis through intramolecular proton transfer and sulfur-oxygen bond formation

Journal of the American Chemical Society

Volumn 119, Issue 34, 1997, Pages 8000-8011

  Bobrowski, Krzysztof ^a,b   Hug, Gordon L ^b   Marciniak, Bronislaw ^b,c   Miller, Brian ^d   Schöneich, Christian ^d  

^a INSTITUTE OF NUCLEAR CHEMISTRY AND TECHNOLOGY   (Poland)

^b UNIVERSITY OF NOTRE DAME   (United States)

^c ADAM MICKIEWICZ UNIVERSITY   (Poland)

^d UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SULFIDE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; ELECTRON TRANSPORT; OXIDATION; PHOTOLYSIS; PHOTOOXIDATION; PROTON TRANSPORT;

EID: 0030817630     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja970683r     Document Type: Article

References (53)

1. Manning, M. C.; Patel, K.; Borchardt, R. T. Pharm. Res. 1989, 6, 903-918.
2. Glass, R. S.; Hojjatie, M.; Wilson, G. S.; Mahling, S.; Göbl, M.; Asmus, K.-D. J. Am. Chem. Soc. 1984, 106, 5382-5383.
3. Asmus, K.-D.; Göbl, M.; Hiller, K.-O.; Mahling, S.; Mönig, J. J. Chem. Soc., Perkin Trans. 2 1985, 641-646.
4. Mahling, S.; Asmus, K.-D.; Glass, R. S.; Hojjatie, M.; Wilson, G. S. J. Org. Chem. 1987, 52, 3717-3724.
5. Steffen, L. K.; Glass, R. S.; Sabahi, M.; Wilson, G. S.; Schöneich, C.; Mahling, S.; Asmus, K.-D. J. Am. Chem. Soc. 1991, 113, 2141-2145.
6. Schöneich, C.; Zhao, F.; Madden, K. P.; Bobrowski, K. J. Am. Chem. Soc. 1994, 116, 4641-4652.
7. Bobrowski, K.; Schöneich, C.; Holcman, J.; Asmus, K.-D. J. Chem. Soc., Perkin Trans. 2 1991, 353-362.
8. Bobrowski, K.; Schöneich, C.; Holcman, J.; Asmus, K.-D. J. Chem. Soc., Perkin Trans. 2 1991, 975-980.
9. Bobrowski, K.; Schöneich, C. Radiat. Phys. Chem. 1996, 47, 507-510.
10. Bobrowski, K.; Schöneich, C. Unpublished results.
11. Bobrowski, K.; Pogocki, D.; Hug, G. L.; Schöneich, C. 1997, manuscript in preparation.
12. Bobrowski, K.; Hug, G. L.; Marciniak, B. Unpublished results.
13. Schöneich, C.; Bobrowski, K. J. Am. Chem. Soc. 1993, 115, 6538-6547.
14. Lucia, L. A.; Burton, R. D.; Schanze, K. S. J. Phys. Chem. 1993, 97, 9078-9080.
15. Baciocchi, E.; Bietti, M.; Putignani, L.; Steenken, S. J. Am. Chem. Soc. 1996, 118, 5952-5960.
16. Guttenplan, J. B.; Cohen, S. G. J. Org. Chem. 1973, 38, 2001-2007.
17. Bobrowski, K.; Marciniak, B.; Hug, G. L. J. Photochem. Photobiol., A 1994, 81, 159-168.
18. Marciniak, B.; Bobrowski, K.; Hug, G. L.; Rozwadowski, J. J. Phys. Chem. 1994, 98, 4854-4860.
19. Bobrowski, K.; Marciniak, B.; Hug, G. L. J. Am. Chem. Soc. 1992, 114, 10279-10288.
20. Marciniak, B.; Bobrowski, K.; Hug, G. L. J. Phys. Chem. 1993, 97, 11937-11943.
21. Bobrowski, K.; Hug, G. L.; Marciniak, B.; Kozubek, H. J. Phys. Chem. 1994, 98, 537-544.
22. Marciniak, B.; Hug, G. L.; Bobrowski, K.; Kozubek, H. J. Phys. Chem. 1995, 99, 13560-13568.
23. Encinas, M. V.; Scaiano, J. C. J. Am. Chem. Soc. 1979, 101, 2146-2152.
24. Nagarajan, V.; Fessenden, R. W. J. Phys. Chem. 1985, 89, 2330-2335.
25. Hug, G. L.; Marciniak, B.; Bobrowski, K. J. Phys. Chem. 1996, 100, 14914-14921.
26. Janata, E.; Schuler, R. H. J. Phys. Chem. 1982, 86, 2078-2084.
27. Schuler, R. H. Chem. Educ. 1985, 2, 34-37.
28. Wang, Y. 1993, Unpublished report.
29. Murov, S. L.; Carmichael, I.; Hug, G. L. Handbook of Photochemistry, 2nd ed.; Dekker: New York, 1993.
30. Encinas, M. V.; Wagner, P. J.; Scaiano, J. C. J. Am. Chem. Soc. 1980, 102, 1357-1360.
31. Bonifacic, M.; Möckel, H.; Bahnemann, D.; Asmus, K.-D. J. Chem. Soc., Perkin Trans. 2 1975, 675-685.
32. Carmichael, I. 1997, private communication.
33. Hiller, K.-O.; Masloch, B.; Göbl, M.; Asmus, K.-D. J. Am. Chem. Soc. 1981, 103, 2734-2743.
34. Göbl, M.; Bonifacic, M.; Asmus, K.-D. J. Am. Chem. Soc. 1984, 106, 5984-5988.
35. Mohan, H.; Mittal, J. P. Radiat. Phys. Chem. 1991, 38, 45-50.
36. Mohan, H.; Mittal, J. P. J. Chem. Soc., Perkin Trans. 2 1992, 207-212.
37. Chaudhri, S. A.; Mohan, H., Anklam, E.; Asmus, K.-D. J. Chem. Soc., Perkin Trans. 2 1996, 383-390.
38. Schuler, R. H.; Hartzell, A. L.; Behar, B. J. Phys. Chem. 1981, 85, 192-199.
39. Glass, R. S.; Hojjatie, M.; Petsom, A.; Wilson, G. S.; Göbl, M.; Mahling, S.; Asmus, K.-D. Phosphorus Sulfur 1985, 23, 143-168.
40. Bevington, P. R. Data Reduction and Error Analysis for the Physical Sciences; McGraw-Hill: New York, 1969.
41. Inbar, S.; Linschitz, H.; Cohen, S. G. J. Am. Chem. Soc. 1981, 103, 7323-7328.
42. Hurley, J. K.; Sinai, N.; Linschitz, H. Photochem. Photobiol. 1983, 38, 9-14.
43. Hurley, J. K.; Linschitz, H.; Treinin, A. J. Phys. Chem. 1988, 92, 5151-5159.
44. Mohan, H. J. Chem. Soc., Perkin Trans. 2 1990, 1821-1824.
45. Bobrowski, K.; Holcman, J. J. Phys. Chem. 1989, 93, 6381-6387.
46. Lutz, H.; Breheret, E.; Lindqvist, L. J. Phys. Chem. 1973, 77, 1758-1762.
47. Carmichael, I.; Hug, G. L. J. Phys. Chem. Ref. Data 1986, 15, 1-250.
48. Hug, G. L.; Marciniak, B.; Bobrowski, K. J. Photochem. Photobiol. A 1996, 95, 81-88.
49. Scaiano, J. C. J. Photochem. 1973, 2, 81-118.
50. Schowen, R. L. In Progress in Physical Organic Chemistry; Streitwieser, A., Jr.; Taft, R. W., Eds.; Wiley: New York, 1972; Vol. 9, pp 275-332.
51. Schowen, K. B. J. In Transition States of Biological Processes; Gandour, R. D.; Schowen, R. L., Eds.; Plenum Press: 1978; pp 225-283.
52. Wisniowski, P.; Hug, G. L.; Bobrowski, K. Manuscript in preparation.
53. Asmus, K.-D.; Möckel, H.; Henglein, A. J. Phys. Chem. 1973, 77, 1218-1221.