Inter- and intramolecular pathways for the formation of tetrahydrofurans from β-(phosphatoxy)alkyl radicals. Evidence for a dissociative mechanism

Journal of Organic Chemistry

Volumn 65, Issue 2, 2000, Pages 523-529

  Crich, David ^a   Huang, Xianhai ^a   Newcomb, Martin ^b  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^b WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

TETRAHYDROFURAN DERIVATIVE;

ARTICLE; MOLECULAR INTERACTION; PHOTOLYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034723342     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991570o     Document Type: Article

References (26)

1. Beckwith, A. L. J.; Crich, D.; Duggan, P. J.; Yao, Q. Chem. Rev. 1997, 97, 3273.
2. Zipse, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 1985.
3. Zipse, H. J. Chem. Soc., Perkin Trans. 2 1997, 2691.
4. Zipse, H. Acc. Chem. Res. 1999, 32, 571.
5. Choi, S.-Y.; Crich, D.; Horner, J. H.; Huang, X.; Martinez, F. N.; Newcomb, M.; Wink, D. J.; Yao, Q. J. Am. Chem. Soc. 1998, 120, 211.
6. Crich, D.; Gastaldi, S. Tetrahedron Lett. 1998, 39, 9377.
7. Whitted, P. O.; Horner, J. H.; Newcomb, M.; Huang, X.; Crich, D. Org. Lett. 1999, 1, 153.
8. Newcomb, M.; Horner, J. H.; Whitted, P. O.; Crich, D.; Huang, X.; Yao, Q.; Zipse, H. J. Am. Chem. Soc. 1999, 121, 10685.
9. Crich, D.; Huang, X.; Newcomb, M. Org. Lett. 1999, 1, 225.
10. Giese, B.; Beyrich-Graf, X.; Burger, J.; Kesselheim, C.; Senn, M.; Schafer, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1742.
11. Walling, C.; Cioffari, A. J. Am. Chem. Soc. 1972, 94, 6064.
12. -1 (see ref 21).
13. Brocks, J. J.; Beckhaus, H.-D.; Beckwith, A. L. J.; Rüchardt, C. J. Org. Chem. 1998, 63, 1935.
14. Johnston, L. J.; Schepp, N. P. J. Am. Chem. Soc. 1993, 115, 6564.
15. Giese, B.; Burger, J.; Kang, T. W.; Kesselheim, C.; Wittmer, T. J. Am. Chem. Soc. 1992, 114, 7322.
16. Barton esters have been formed in the presence of alcohols (for some examples, see: Crich, D.; Quintero, L. Chem. Rev. 1989, 89, 1413); however, it was felt that lactonization would be a serious problem if such a strategy were applied to the present system.
17. Kabasakalian, P.; Townley, E. R.; Yudis, M. D. J. Am. Chem. Soc. 1982, 84, 2716.
18. Kim, S.; Lee, T. A.; Song, Y. Synlett. 1998, 501.
19. Descotes, G.; Soula, J.-C. Bull. Soc. Chim. Fr. 1964, 2636.
20. For general experimental details see ref 21.
21. Choi, S.-Y.; Crich, D.; Horner, J. H.; Huang, X.; Newcomb, M.; Whitted, P. O. Tetrahedron 1999, 55, 3317.
22. Rappoport, I.; Gal, A. J. Chem. Soc., Perkin Trans. 2 1973, 301.
23. Gupton, J. T.; Layman, W. J. J. Org. Chem. 1987, 52, 3683.
24. Kawashima, T.; Ishii, T.; Inamoto, N. Bull. Chem. Soc. Jpn. 1987, 60, 1831.
25. Senda, Y.; Kanto, H.; Itoh, H. J. Chem. Soc., Perkin Trans. 2 1997, 1143.
26. Combret, J.-C.; Larcheveque, M.; Leroux, Y. Bull. Soc. Chim. Fr. 1971, 3501.