Chemistry of Singlet Oxygen. 51. Zwitterionic Intermediates from 2, 4-Hexadienes

Journal of the American Chemical Society

Volumn 110, Issue 21, 1988, Pages 7167-7170

  O'Shea, Kevin E ^a   Foote, Christopher S ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001661442     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00229a035     Document Type: Article

References (14)

1. Review: A. A. Frimer In Singlet Oxygen; A. A. Frimer, Ed.; CRC: Boca Raton, FL, 1985; Vol 2.
2. (a) Manring, L. E.; Kanner, R. C.; Foote, C. S. J. Am. Chem. Soc. 1983, 105, 4707, 4710. (b) Gollnick, K.; Griesbeck, A. Tetrahedron 1984, 40, 3235.
3. (a) Fenical, W.; Kearns, D. R.; Radlick, P. J. Am. Chem. Soc. 1969, 91, 2655, 3396, 7771. (b) Hatsui, T.; Takeshita, H. Bull. Soc. Chem. Jpn. 1980, 53, 2655.
4. Gollnick, K.; Griesbeck, A. Tetrahedron Lett. 1983, 24, 3303.
5. Matsumoto, M.; Dobashi, S.; Kuroda, K.; Kondo, K. Tetrahedron 1985, 41, 2147.
6. δG* ~10.5 kcal/mol. Similar behavior has been reported for an alkoxy-substituted endoperoxide: Clennan, E. J.; Nagraba, K. J. Org. Chem. 1987, 52, 294.
7. Ogilby, P. R.; Foote, C. S. J. Am. Chem. Soc. 1983, 105, 3423.
8. Jensen, F.; Foote, C. S. J. Am. Chem. Soc. 1987, 109, 6376.
9. The longer lifetime of singlet oxygen in deuteriated than protiated solvents is well documented but not completely understood. See: D. R. Kearns In Singlet Oxygen; Wasserman, H. H.; Murray, R. W., Eds.; Academic: New York, 1979.
10. (a) Zhang, J.; Foote, C. S. Tetrahedron Lett. 1986, 27, 6153. (b) Burns, P. A.; Foote, C. S. J. Am. Chem. Soc. 1974, 96, 4339. (c) Hasty, N. M.; Kearns, D. R. J. Am. Chem. Soc. 1973, 95, 3380.
11. (a) Clennan, E. L.; Earlywine, A. D. J. Am. Chem. Soc. 1987, 109, 7104. (b) Cheng, C. C.; Seymour, C. A.; Petti, M. A.; Greene, F. D.; Blount. J. F. J. Org. Chem. 1984, 49, 2910. (c) Seymour, C. A.; Greene, F. D. J. am. Chem. Soc. 1980, 102, 6384. (d) Orfanopoulos, M.; Foote, C. S. Smonou, I. Tetrahedron Lett. 1987, 28, 15. (e) Nelsen, S. F.; Kapp, D. L. J. Am. Chem. Soc. 1985, 107, 5548.
12. (a) Kataoka, F.; Shimizu, N.; Nishida, S. J. Am. Chem. Soc. 1980, 102, 711. (b) Kataoka, F.; Nishida, S.; Tsuji, T.; Marakami, M. J. Am. Chem. Soc. 1981, 103, 6878. (c) Fatiadi, A. J. Synthesis 1987, 749.
13. Salem, L.; Rowland, C. Angew. Chem., Int. Ed. Engl. 1972, 11, 92.
14. McGreer, D. E.; Page, D. B. Can. J. Chem. 1969, 47, 866.