Intramolecular Anodic Olefin Coupling Reactions: A Useful Method for Carbon-Carbon Bond Formation

Journal of the American Chemical Society

Volumn 113, Issue 19, 1991, Pages 7372-7385

  Hudson, Christine M ^a   Marzabadi, Mohammad R ^a   Moeller, Kevin D ^a   New, Dallas G ^a  

^a WASHINGTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000817834     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00019a038     Document Type: Article

References (70)

1. Baizer, M. M. Organic Electrochemistry: An Introduction and a Guide, 2nd ed.; Baizer, M. M., Lund, H., Eds.; M. Dekker: New York, 1983.
2. Torii, S. Electroorganic Synthesis: Methods and Applications: Part I - Oxidations; VCH: Deerfield Beach, FL., 1985.
3. Yoshida, K. Electro-oxidation in Organic Chemistry: The Role of Cation Radicals as Synthetic Intermediates; John Wiley and Sons: New York, 1984.
4. Ross, S. D.; Finkelstein, M.; Rudd, E. J. Anodic Oxidation; Academic Press: New York, 1975.
5. Schaefer, H. J. Angew. Chem., Int. Ed. Engl. 1981, 20, 911.
6. Dombroski, M. A.; Kates, S. A.; Snider, B. B. J. Am. Chem. Soc. 1990, 112, 2759.
7. Kates, S. A.; Dombroski, M. A.; Snider, B. B. J. Org. Chem. 1990, 55, 2427.
8. Snider, B. B.; Patricia, J. J. J. Org. Chem. 1989, 54, 38.
9. Snider, B. B.; Patricia, J. J.; Kates, S. A. J. Org. Chem. 1988, S3, 2137.
10. Snider, B. B.; Dombroski, M. A. J. Org. Chem. 1987, 52, 5487.
11. Mohan, R.; Kates, S. A.; Dombroski, M. A.; Snider, B. B. Tetrahedron Lett. 1987, 28, 845.
12. Snider, B. B.; Mohan, R.; Kates, S. A. Tetrahedron Lett. 1987, 28, 841.
13. Snider, B. B.; Mohan, R.; Kates, S. A. J. Org. Chem. 1985, 50, 3659.
14. Corey, E. J.; Ghosh, A. K. Tetrahedron Lett. 1987, 28, 175.
15. Corey, E. J.; Gross, A. W. Tetrahedron Lett. 1985, 26, 4291.
16. Corey, E. J.; Kang, M. J. Am. Chem. Soc. 1984, 106, 5384.
17. Fristad, W. E.; Peterson, J. R.; Ernst, A. B.; Urbi, G. B. Tetrahedron 1986, 42, 3429.
18. Fristad, W. E.; Hershberger, S. S. J. Org. Chem. 1985, 50, 1026.
19. Fristad, W. E.; Peterson, J. R.; Ernst, A. B. J. Org. Chem. 1985, 80, 3143.
20. Fristad, W. E.; Peterson, J. R. J. Org. Chem. 1985, 50, 10.
21. Fristad, W. E.; Ernst, A. B. Tetrahedron Lett. 1985, 26, 3761.
22. Pattenden, G.; Bhandal, H.; Russell, J. J. Tetrahedron Lett. 1986, 27, 2299.
23. Pattenden, G.; Patel, V. F.; Russell, J. J. Tetrahedron Lett. 1986, 27, 2303.
24. Breslow, R.; Olin, S. S.; Groves, J. T. Tetrahedron Lett. 1968, 15, 1837.
25. Kraus, G. A.; Landgrebe, K. Tetrahedron Lett. 1984, 25, 3939.
26. Baldwin, J. E.; Li, C. S. J. Chem. Soc., Chem. Commun. 1987, 166.
27. Curran, D. P.; Chang, C. T. J. Org. Chem. 1989, 54, 3140.
28. Schaefer, H. J. Angew. Chem., Int. Ed. Engl. 1981, 20, 911.
29. Yamamura, S.; Shizuri, Y.; Nakamura, K. J. Chem. Soc., Chem. Commun. 1985, 530.
30. Yoshida, J.; Sakaguchi, K.; Isoe, S. J. Org. Chem. 1988, S3, 2525
31. Yoshida, J.; Sakaguchi, K.; Isoe, S. Tetrahedron Lett. 1986, 27, 6075.
32. Holze, R.; Hamann, C. H. Tetrahedron 1991, 47, 737.
33. Amatore, C.; Moustafid, T. E.; Rolando, C.; Verpeaux, J. N. Tetrahedron 1991, 47, 777.
34. Chapuzet, J. M.; Simonet, J. Tetrahedron 1991, 47, 791.
35. Swenton, J. S.; Morrow, G. W. Tetrahedron Lett. 1987, 28, 5445.
36. Morrow, G. W.; Chen, Y.; Swenton, J. S. Tetrahedron 1991, 47, 655.
37. Becking, L.; Schaefer, H. J. Tetrahedron Lett. 1988, 29, 2797.
38. Yamamura, S.; Shizuri, Y.; Okuno, Y.; Shigemori, H. Tetrahedron Lett. 1987, 28, 6661.
39. Yamamura, S.; Shizuri, Y.; Shigemori, H.; Okuno, Y.; Ohkubo, M. Tetrahedron 1991, 47, 635.
40. Swanson, K. L.; Snow, K. M.; Jeyakumar, D.; Smith, K. M. Tetrahedron 1991, 47, 685.
41. Shono, T.; Nishiguchi, I.; Kashimura, S.; Okawa, M. Bull. Chem. Soc. Jpn. 1978, 51, 2181.
42. Belleau, B.; Au-Young, Y. K. Can. J. Chem. 1969, 47, 2117.
43. Fritsch, J. M.; Weingarten, H. J. Am. Chem. Soc. 1968, 90, 793.
44. Fritsch, J. M.; Weingarten, H.; Wilson, J. D. J. Am. Chem. Soc. 1970, 92, 4038.
45. Le Moing, M. A.; Le Guillanton, G.; Simonet, J. Electrochim. Acta 1981, 26, 139.
46. Engels, R.; Schaefer, H. J.; Steckhan, E. Liebigs Ann. Chem. 1977, 204.
47. Schaefer, H. J.; Steckhan, E. Tetrahedron Lett. 1970, 44, 3835.
48. Schaefer, H. J.; Steckhan, E. Angew. Chem., Int. Ed. Engl. 1974, 13, 472.
49. Koch, D.; Schaefer, H. J.; Steckhan, E. Chem. Ber. 1974, 107, 3640.
50. Fox, M. A.; Akaba, R. J. Am. Chem. Soc. 1983, 103, 3460.
51. Moeller, K. D.; Tinao, L. V. Electroorganic Synthesis - Festschrift in Honor of Manuel M. Baizer, Little, R. D., Weinberg, N. L., Eds.; Marcel Dekker: New York, 1991; p 153.
52. Moeller, K. D.; Marzabadi, M. R.; New, D. G.; Chiang, M. Y.; Keith, S. J. Am. Chem. Soc. 1990, 112, 6123.
53. Dolson, M. G.; Swenton, J. S. J. Am. Chem. Soc. 1981, 103, 2361
54. Nilsson, A.; Palmquist, U.; Pettersson, T.; Ronlan, A. J. Chem. Soc, Perkin Trans. 1 1978, 7, 708.
55. Phelps, J.; Santhanam, K. S. V.; Bard, A. J. J. Am. Chem. Soc. 1967, 89, 1752.
56. Snider, B. B.; Kwon, T. J. Org. Chem. 1990, 55, 4786.
57. Schinzer, D. Synthesis 1988, 263
58. Fleming, I. In Comprehensive Organic Chemistry; Jones, D. N., Ed.; Pergamon Press: Oxford, 1979; Vol. 3, p 541.
59. Yoshida, J.; Murata, T.; Isoe, S. Tetrahedron Lett. 1986, 27, 3373.
60. Koizumi, T.; Fuchigami, T.; Nonaka, T. Bull. Chem. Soc. Jpn. 1989, 62, 219.
61. Tu, C. L.; Mariano, P. S. J. Am. Chem. Soc. 1987, 109, 5287.
62. Mizuno, K.; Yasueda, M.; Otsuji, Y. Chem. Lett. 1988, 229.
63. Moeller, K. D.; Hudson, C. M. Tetrahedron Lett. 1991, 32, 2307.
64. Ireland, R. E.; Norbeck, D. W. J. Org. Chem. 1985, 50, 2198.
65. Baizer, M. M. Organic Electrochemistry: An Introduction and a Guide, 2nd ed.; Baizer, M. M., Lund, H., Eds.; M. Dekker: New York, 1983; p 183.
66. Brennan, M. P. J.; Brettle, R. J. Chem. Soc., Perkin Trans. 1 1973, 257.
67. Moeller, K. D.; Wang, P. W.; Tarazi, S.; Marzabadi, M. R.; Wong, P. L. J. Org. Chem. 1991, 56, 1058.
68. Kinney, R. J.; Jones, W. D.; Bergman, R. G. J. Am. Chem. Soc. 1978, 100, 7902.
69. Seyfreth, D.; Worsthorn, K. R.; Mammarella, R. E. J. Org. Chem. 1977, 42, 3104.
70. Hemming, I.; Paterson, I. Synthesis 1979, 445.