Photochemical smiles rearrangement and meisenheimer complex formation catalyzed by hydroxide ion via electron hole transfer catalysis

Organic Letters

Volumn 7, Issue 21, 2005, Pages 4741-4744

  Wubbels, Gene G ^a   Ota, Nobutoshi ^a   Crosier, Michelle L ^b  

^a UNIVERSITY OF NEBRASKA AT KEARNEY   (United States)

^b WASHINGTON COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 27144541195     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol051941p     Document Type: Article

References (32)

1. Karapire, C.; Icli, S. In Organic Photochemistry and Photobiology, 2nd ed.; Horspool, W., Lenci, F., Eds.; CRC Press: Boca Raton, 2004; Chapter 37, pp 37-1-37-14.
2. (a) Zimmerman, H. E.; Somasekhara, S. J. Am. Chem. Soc. 1963, 85, 922.
3. (b) Zimmerman, H. E. J. Phys. Chem. A 1998, 102, 5616.
4. (a) de Bie, D. A.; Havinga, E. Tetrahedron 1965, 21, 2359.
5. (b) Huck, L. A.; Wan, P. Org. Lett. 2004, 6, 1797.
6. Wubbels, G. G.; Snyder, E. J.; Coughlin, E. B. J. Am. Chem. Soc. 1988, 110, 2543.
7. (a) Fang, K.; Hashimoto, M.; Jockusch, S.; Turro, N. J.; Nakanishi, K. J. Am. Chem. Soc. 1998, 120, 8543.
8. (b) Specht, A.; Goeldner, M. Angew. Chem., Int. Ed. 2004, 43, 2008.
9. (a) Matsui, K.; Maeno, N.; Suzuki, S.; Shizuka, H.; Morita, T. Tetrahedron Lett. 1970, 1467.
10. (b) Mutai, K.; Kanno, S.; Kobayashi, K. Tetrahedron Lett. 1978, 1273.
11. (c) Wubbels, G. G.; Halverson, A. M.; Oxman, J. D. J. Am. Chem. Soc. 1980, 102, 4848.
12. Mutai, K.; Nakagaki, R. Bull. Chem. Soc. Jpn. 1985, 58, 3663.
13. Wubbels, G. G.; Winitz, S.; Whitaker, C. J. Org. Chem. 1990, 55, 631.
14. Knipe, A. C.; Lound-Keast, J.; Sridhar, N. Chem. Commun. 1976, 765.
15. (a) Wubbels, G. G.; Celander, D. W. J. Am. Chem. Soc. 1981, 103, 7669.
16. (b) Wubbels, G. G. Acc. Chem. Res. 1983, 16, 286.
17. (c) Wubbels, G. G.; Cotter, W. D.; Sanders, H.; Pope, C. J. Org. Chem. 1995, 60, 2960.
18. de Jongh, R. O.; Havinga, E. Recl. Trav. Chim. Pays-Bas 1966, 85, 275.
19. Bunce, N. J.; LaMarre, J.; Vaish, S. P. Photochem. Photobiol. 1984, 39, 531.
20. Terrier, F. Nucleophilic Aromatic Displacement: The Influence of the Nitro Group; VCH Publishers: New York, 1991; Chapter 2.
21. Reference 13, pp 42, 108, and 272.
22. Wubbels, G. G.; van Zeijl, P. H. M.; Varma, C. A. G. O. Abstracts of Papers. 185th National ACS Meeting; Seattle, WA, March 1983; American Chemical Society: Washington, DC, 1983.
23. van Zeijl, P. H. M.; van Eijk, L. M. J.; Varma, C. A. G. O. J. Photochem. 1985, 29, 415.
24. Varma, C. A. G. O.; Tamminga, J. J.; Cornelisse, J. J. Chem. Soc., Faraday Trans. 2 1982, 78, 265.
25. Loeff, I.; Treinin, A.; Linschitz, H. J. Phys. Chem. 1983, 87, 2536.
26. 1 (triplet decay) goes not only back to starting material but also to other photoproducts. Since amide ions have negligible leaving group ability, the σ-complex in Scheme 1 can go only to 3 in alkaline media.
27. Collado, D.; Perez-Inestrosa, E.; Suau, R. J. Org. Chem. 2003, 68, 3574.
28. Simic, M.; Neta, P.; Hayon, E. Int. J. Radiat. Phys. Chem. 1971, 3, 309.
29. Wubbels, G. G.; Sevetson, B. R. J. Phys. Org. Chem. 1989, 2, 177.
30. Wubbels, G. G.; Jordan, J. W.; Mills, N. S. J. Am. Chem. Soc. 1973, 95, 1281.
31. Wubbels, G. G.; Monaco, W. J.; Johnson, D. E.; Meredith, R. S. J. Am. Chem. Soc. 1976, 98, 1036.
32. Wubbels, G. G.; Kalhorn, T. F.; Johnson, D. E.; Campbell, D. J. Org. Chem. 1982, 47, 4664.