Reactions of singlet oxygen and N-methyltriazolinediones with β,β-dimethylstyrene. exceptional syn selectivity in the ene products

Journal of Organic Chemistry

Volumn 63, Issue 4, 1998, Pages 1315-1318

  Stratakis, Manolis ^a,b   Orfanopoulos, Michael ^a   Foote, Christopher S ^a,b  

^a UNIVERSITY OF CRETE   (Greece)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001190623     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo9715332     Document Type: Article

References (38)

1. Stephenson, L. M.; Grdina, M. B.; Orfanopoulos, M. Ace. Chem. Res. 1980, 13, 419-425.
2. (a) Seymour, C. A.; Greene, F. D. J. Am. Chem. Soc. 1980, 102, 6384-6385.
3. (b) Orfanopoulos, M.; Smonou, I.; Foote, C. S. J. Am. Chem. Soc. 1990, 112, 3607-3614.
4. (c) Squillacote, M.; Mooney, M.; De Felippis, J. J. Am. Chem. Soc. 1990, 112, 5364-5365.
5. (d) Poon, T. H. W.; Park, S. H.; Elemes, Y.; Foote, C. S. J. Am. Chem. Soc. 1995, 117, 10468-10473.
6. (a) Orfanopoulos, M.; Grdina, M. B.; Stephenson, L. M. J. Am. Chem. Soc. 1979, 101, 275-276.
7. (b) Schulte-Elte, K. H.; Rautenstrauch, V. J. Am. Chem. Soc. 1980, 102, 1738-1740.
8. (a) Rousseau, G.; Le Perchec, P.; Conia, J. M. Tetrahedron Lett. 1977, 2517-20.
9. (b) Lerdal, D.; Foote, C. S. Tetrahedron Lett. 1978, 3227-3230.
10. (a) Stephenson, L. M. Tetrahedron Lett. 1980, 21, 1005-08.
11. (b) Hurst, J. R.; Schuster, G. B. J. Am. Chem. Soc. 1982, 104, 6854-6856.
12. (c) Hurst, J. R.; Wilson, S. L.; Schuster, G. B. Tetrahedron 1985, 41, 2191-2197.
13. ) Stratakis, M.; Orfanopoulos, M. Tetrahedron Lett. 1995, 36, 4291-4294.
14. Cheng, C. C.; Seymour, CA.; Petti, M. A.; Greene, F. D.; Blount, J. F. J. J. Org. Chem. 1984, 49, 2910-2916.
15. (a) Orfanopoulos, M.; Stratakis, M .; Elemes, Y. Tetrahedron Lett. 1989, 30, 4875-4878.
16. (b) Elemes, Y.; Stratakis, M.; Orfanopoulos, M. Tetrahedron Lett. 1989, 30, 6903-6906.
17. (a) Orfanopoulos, M.; Stratakis, M.; Elemes, Y. J. Am. Chem. Soc. 1990, 112, 6417-6419.
18. (b) Orfanopoulos, M.; Elemes, Y.; Stratakis, M. Tetrahedron Lett. 1990, 31, 5775-5778.
19. (c) Clennan, E. L.; Chen, X.; Koola, J. J. J. Am. Chem. Soc. 1990, 112, 5193-5199.
20. (d) Clennan, E. L.; Koola, J. J.; Oolman, K. A. Tetrahedron Lett. 1990, 31, 6759- 6762.
21. Orfanopoulos, M.; Stratakis, M.; Elemes, Y.; Jensen, F. J. Am. Chem. Soc. 1991, 113, 3180-3181.
22. (a) Adam, W.; Nestler, B. J. Am. Chem. Soc. 1992, 114, 6549-6550.
23. (b) Adam, W.; Nestler, B. J. Am. Chem. Soc. 1993, 115, 5041-5049.
24. (a) Adam, W.; Briinker, H.-G. J. Am. Chem. Soc. 1993, 115, 3008-3009.
25. (b) Brünker, H.-G.; Adam, W. J. Am. Chem. Soc. 1995, 117, 3976-3982.
26. Adam, W.; Brünker, H .-G.; Kumar, A. S.; Peters, E.-M .; Peters, K.; Schneider, U.; von Schnering, H. G. J. Am. Chem. Soc. 1996, 118, 1899-1905.
27. Stratakis, M.; Orfanopoulos, M.; Foote, C. S. Tetrahedron Lett. 1996, 37, 7159-7162.
28. (a) Matsumoto, M.; Dobashi, S.; Kuroda, K. Tetrahedron Lett. 1977, 3361-3364.
29. (b) Matsumoto, M.; Kuroda, K. Synth. Commun. 1981, 11, 987-992.
30. ) Grdina, M. B.; Orfanopoulos, M.; Stephenson, L. M. J. Org. Chem. 1979, 44, 2936-2938.
31. Stratakis, M.; Orfanopoulos, M.; Chen, J. S.; Foote, C. S. Tetrahedron Lett. 1996, 37, 4105-4108.
32. Jensen, F.; Foote, C. S. J. Am. Chem. Soc. 1987, 109, 6376-6385.
33. Smonou, I.; Orfanopoulos, M.; Foote, C. S. Tetrahedron Lett. 1988, 29, 2769-2772.
34. Smonou, I.; Khan, S.; Foote, C. S.; Elemes, Y.; Mavridis, I. M.; Pantidou, A.; Orfanopoulos, M. J. Am. Chem. Soc. 1995, 117, 7081-7087.
35. Similar inverse intramolecular isotope effect have been measured in the reaction of PTAD with trimethylethylene. Elemes Y.; Orfanopoulos, M., unpublished results.
36. Preliminary studies have shown that MTAD addition to the p-methyl derivative of 1 affordstheene product exclusively. Even with the p-methoxy derivative, where the p-methoxybenzyl cation is far more stable than the tertiary alkyl, there is a significant amount of ene product (∼20%), along with several other adducts, including [2 + 2] and [4 + 2] products. Stratakis, M.; Hadjimarinaki, M.; Orfanopoulos, M., unpublished results.
37. Brittelli, D. R. J. Org. Chem. 1981, 46, 2514-2520.
38. Higgins, R.; Foote, C. S.; Cheng, H . ACS Adv. Chem. Ser. 1968, 77, 102.