Mechanism of the Ene Reaction Between Singlet Oxygen and Olefins

Accounts of Chemical Research

Volumn 13, Issue 11, 1980, Pages 419-425

  Stephenson, L M ^a   Grdina, Mary Jo ^b   Orfanopoulos, Michael ^b  

^a UNIVERSITY OF SOUTHERN CALIFORNIA   (United States)

^b CASE WESTERN RESERVE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33749630227     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar50155a006     Document Type: Article

References (58)

1. Childs, W. H. J.; Mecke, R. Z. Physik 1974, 68, 334.
2. Schenck, G. O.; Schulte-Elte, K. Liebigs Ann. Chem., 1958, 618, 185.
3. Schenck, G. O.; Ziegler, K. Naturwissenschaften 1945, 32, 157.
4. Bartlett, P. D.; Schaap, A. P. J. Am. Chem. Soc. 1970, 92, 3223, 6055.
5. Denny, R. W.; Nickon, A. Org., React. 1973, 20, 133.
6. Gollnick, K.; Kuhn, H. J. In “Singlet Oxygen”, Wasserman, H. H., Murray, R. W., Eds.; Academic Press: New York, 1979, p 287.
7. Foote, C. S. Acc. Chem, Res. 1968, 11, 104.
8. Ranby, B Rabek, J. F., Eds. “Singlet Oxygen Reactions with Organic Compounds and Polymers”, Wiley: New York, 1978.
9. Pitts, J. N., Jr., Ann. N.Y. Acad. Sci. 1970, 171, 239.
10. Khan, A. U.; Kasha, M. Ann. N.Y. Acad. Sci. 1970, 171, 24.
11. Kearns, D. R. Chem. Rev. 1971, 71, 395, 424.
12. Kasha, M.; Khan, A. U. Ann. N.Y. Acad. Sci. 1970, 171, 5.
13. Foote, C. S. Pure Appl. Chem. 1971, 27, 635.
14. Kopecky, K. R.; Van de Sande, J. H. Can. J. Chem. 1972, 50, 4034.
15. Nickon, A.; Chuang, V. T.; Daniels, P. J. L.; Denny, R. W.; DiGiorgio, J. B.; Tsunetsugu, J.; Vilhuber H. G.; Werstink, E. J. Am. Chem. Soc. 1972, 94, 5517.
16. Foote, C. S.; Wexler, S.; Ando, W. Tetrahedron Lett. 1965, 4111.
17. Litt, F. A.; Nickon, A. Adv. Chem. Ser. 1968, No. 77, 118.
18. Gollnick, K.; Schenck, G. O. Pure Appl. Chem. 1964, 9, 507.
19. Foote, C. S. Science 1968, 162, 963.
20. Gollnick, K. Adv, Chem. Ser. 1968, No. 77, 78.
21. Gollnick, K. Adv. Photochem. 1968, 6, 1.
22. Kearns, D. R.; Fenical, W.; Radlick, P. Ann. N. Y. Acad. Sei. 1970, 171, 34.
23. Harding, L. B.; Goddard, W. A., III. J. Am. Chem. Soc. 1977, 99, 4520.
24. Harding, L. B.; Goddard, W. A. III. Tetrahedron Lett. 1978, 747.
25. Harding, L. B.; Goddard, W. A. III. J. Am. Chem. Soc., 1980, 102, 439.
26. Litt, F. A.; Nickon, A. Adv. Chem. Ser. 1968, No. 77, 118.
27. Jefford, C. W. Tetrahedron Lett. 1979, 985.
28. Jefford, C. W.; Rimbault, C. G. J. Am. Chem. Soc. 1978, 100, 295.
29. Jefford, C. W.; Laffer, M. H.; Boschung, A. F. J. Am. Chem. Soc, 1972, 94, 8904.
30. Jefford, C. W.; Rimbault, C. G. J. Org. Chem. 1978, 43, 1908.
31. Jefford, C. W.; Boschung, A. F. Helv. Chim. Acta 1974, 57, 2242.
32. Rousseau, G.; LaPerchec, P.; Conia, J. M. Tetrahedron Lett. 1977, 2517.
33. Sharp, D. B., “Abstracts of Papers”, 138th National Meeting, American Chemical Society: Washington, DC, 1960; p 79p.
34. Dewar, M. J. S.; Thiel, W. J. Am. Chem. Soc. 1975, 97, 3978.
35. Dewar, M. J. S.; Thiel, W. J. Am. Chem. Soc. 1977, 99, 2338.
36. Dewar, M. J. S.; Griffin, A. C.; Thiel, W.; Turchi, I. J. J. Am. Chem. Soc. 1975, 97, 4339.
37. Frimer, A. A.; Bartlett, P. D.; Boschung, A. F.; Jewett, J. G. J. Am. Chem. Soc. 1975, 97, 4339.
38. Orfanopoulos, M. G. Ph.D. Thesis, 1979, Case Western Reserve University.
39. Orfanopoulos, M. G.; Grdina, M. B.; Stephenson, L. M. J. Am. Chem. Soc. 1979, 101, 275.
40. Lerdal, D.; Foote, C. S. Tetrahedron Lett. 1978, 3227.
41. Schulte-Elte, K. H.; Muller, B. L.; Rautenstrauch, V. Helv. Chim. Acta 1978, 61, 2777.
42. Schulte-Elte, K. H.; Muller, B. L.; Pamingle, H. Helv. Chim. Acta 1979, 62, 816.
43. Schulte-Elte, K. H.; Rautenstrauch, V. J. Am. Chem. Soc. in press.
44. Kopecky, K. R.; Reich, H. H. Can J. Chem. 1965, 43, 2265.
45. Paquette, L. A.; Liotta, D. C.; Baker, A. D. Tetrahedron Lett. 1976, 2681.
46. Stephenson, L. M.; Mattem, D. L. J. Org. Chem. 1976, 41, 3614.
47. Gollnick, K.; Hartmann, H. Conference Abstracts, International Conference on Oxygen and Oxy-Radicals in Chemistry and Biology, University of Texas: Austin, Texas, May 25-29, 1980.
48. Stephenson, L. M.; McClure, D. E.; Sysak, P. K. J. Am. Chem. Soc. 1973, 95, 7888.
49. Orfanopoulos, M. G.; Stephenson, L. M. J. Am. Chem. Soc. 1980, 102, 1417.
50. Kopecky, K. R.; Van de Sande, J. H. Can. J. Chem. 1972, 50, 4034.
51. Grdina, M. B. Ph.D. Thesis, 1979, Case Western Reserve University.
52. Grdina, M. B.; Orfanopoulos, M.; Stephenson, L. M. J. Am. Chem. Soc. 1979, 1011, 3111.
53. Seymour, C. A.; Greene, F. D. J. Am. Chem. Soc., in press.
54. Keams, D. R.; Fenical, W.; Radlick, P. Ann. N.Y. Acad. Sci. 1970, 171, 34.
55. Inagaki, S.; Fujimoto, H.; Fukui, K. Chem. Lett. 1976, 749.
56. Inagaki, S.; Fukui, K. J. Am. Chem. Soc. 1975, 97, 7480.
57. McClure, D. E. Ph.D. Thesis, 1973, Stanford University.
58. Caldwell, R. A.; Creed, D. Acc. Chem, Res, 1980, 13, 45, 50.