A novel pathway in the photooxygenation of cyclic allenes

Organic Letters

Volumn 2, Issue 10, 2000, Pages 1383-1385

  Erden, Ihsan ^a   Song, Jiangao ^a   Cao, Weiguo ^a  

^a SAN FRANCISCO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; HYDROCARBON; OXYGEN; SINGLET OXYGEN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; PHOTOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

ALKENES; HYDROCARBONS, CYCLIC; MOLECULAR STRUCTURE; OXYGEN; PHOTOCHEMISTRY; SINGLET OXYGEN; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0034682160     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol005692a     Document Type: Article

References (35)

1. For reviews, see: (a) Schaap, A. P.; Zaklika, K. A. In Singlet Oxygen; Wasserman, H. H., Murray, R. W., Eds.; Academic Press: New York, 1979; pp 173-242.
2. (b) Bartlett, P. D.; Landis, M. E. In Singlet Oxygen; Wasserman, H. H., Murray, R. W., Eds.; Academic Press: New York 1979; pp 243-286.
3. (c) Frimer, A. A. In The Chemistry of Peroxides; Patai, S., Ed.; Wiley & Sons: New York, 1983; p 201.
4. Greibrokk, T. Tetrahedron Lett. 1973, 1663.
5. (a) Gollnick, K.; Schnatterer, A. Tetrahedron Lett. 1985, 26, 5029.
6. (b) Gollnick, K.; Schnatterer, A. Tetrahedron Lett. 1985, 26, 173.
7. (c) Martinez, T. R. M.S. Thesis, San Francisco State University, San Francisco, CA, 1986.
8. The Chemistry of Allenes; Landor, S. R., Ed.; Academic Press: New York, 1982; Vols. 1-3.
9. Erden, I.; Martinez, T. R. Tetrahedron Lett. 1991, 32, 1859.
10. Minute amounts (ca. 5%) of the corresponding "ene" products, hydroxyenones and dienones, are also formed in each case, along with polymeric material.
11. Quannès, C.; Wilson, T. J. Am. Chem. Soc. 1968, 90, 6528.
12. (a) Sara-Moeller, C. R.; Adam, W. In Four-membered Rings with Two Oxygen Atoms: Dioxetanes; Katritzky, A. R., Rees, C. W. E., Scriven, F., Eds.; Comprehensive Heterocyclic Chemistry, 2nd ed. (CHEC-2); Elsevier: 1996; Vol. 1, Chapter 1.33, pp 1041-1082.
13. (b) Adam, W. In The Chemistry of Functional Groups, Peroxides, Four-membered Ring Peroxides: 1,2-Dioxetanes and α-Peroxylactones; Patai, S., Ed.; Wiley & Sons: New York, 1983; Chapter 24, pp 830-920.
14. (a) Rubin, M. B. Chem Rev. 1975, 75, 177.
15. (b) de Neufville, R.; von Pechmann, H. Ber. Dtsch. Chem. Ges. 1890, 23, 3375.
16. Scott, L. T.; Erden, I.; Brunsvold, W. R.; Schultz, T. H.; Houk, K. N.; Paddon-Row, M. N. J. Am. Chem. Soc. 1982, 104, 3659.
17. (a) Lee, C. B.; Taylor, D. R. J. Chem. Res., Synop. 1977, 136; J. Chem. Res., Miniprint 1977, 1601.
18. (a) Lee, C. B.; Taylor, D. R. J. Chem. Res., Synop. 1977, 136; J. Chem. Res., Miniprint 1977, 1601.
19. (b) Lee, C. B.; Taylor, D. R. J. Chem. Soc., Perkin Trans. 1 1977, 1463.
20. de Meijere, A.; Erden, I.; Weber, W.; Kaufmann, D. J. Org. Chem. 1988, 53, 152.
21. Gollnick, K.; Kuhn, H. J. In Singlet Oxygen; Wasserman, H. H., Murray, R. W., Eds.; Academic Press: New York, 1979; pp 287-427.
22. (a) Coats, S. J.; Wasserman, H. H. Tetrahedron Lett. 1995, 36, 7735.
23. (b) Wasserman, H. H.; Baldino, C.; Coats, S. J. J. Org. Chem. 1995, 60, 8231.
24. (a) Wasserman, H. H.; Shiraishi, M.; Cook, J. D. Tetrahedron Lett. 1995, 36, 6785.
25. (b) Wasserman, H. H.; Blum, C. A. Tetrahedron Lett. 1994, 35, 9787.
26. (c) Wasserman, H. H.; Lee, G. M. Tetrahedron Lett. 1994, 35, 9783.
27. (c) Wasserman, H. H.; Vu, C. B. Tetrahedron Lett. 1994, 35, 9779.
28. (d) Wasserman, H. H.; Kuo, G.-H. Tetrahedron 1992, 48, 7071 and references therein;
29. (e) For a recent review on vicinal triones, see: Rubin, M. B.; Gleiter, R. Chem Rev. 2000, 100, 1121.
30. (a) Schank, K.; Schuhknecht, C. Chem. Ber. 1982, 115, 3032.
31. (b) Wasserman, H. H.; Pickett, J. E. J. Am. Chem. Soc. 1982, 104, 4695.
32. (c) Mahran, M. R.; Abdou, W. M.; Sidky, M. M.; Wamhoff, H. Egypt. J. Chem. 1987, 29, 701.
33. (d) Tatsugi, J.; Izawa, Y. J. Chem. Res., Synop. 1988, 356.
34. (e) Regitz, M.; Adolph, H. G. Z. Naturforsch. B 1968, 23, 1269.
35. (f) Beck, E.; Hofmann, P.; Sieber, A. Tetrahedron Lett. 1981, 22, 4683.