The kinetic impact of vinylic fluorine substituents on 5-hexenyl radical cyclizations

Tetrahedron Letters

Volumn 37, Issue 30, 1996, Pages 5321-5324

  Dolbier Jr , William R ^a   Rong, Xiao X ^a  

^a University of Florida ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOFLUORINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030598043     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01120-3     Document Type: Article

References (21)

1. 1. Tedder, J. M. Angew. Chem. Int. Ed. Engl. 1982, 27, 401-410.
2. 2. Giese, B. Angew. Chem. Int. Ed. Engl. 1983, 22, 753-764.
3. 3. Beckwith, A.L. J.; Schiesser, C. H. Tetrahedron 1985, 41, 3925-3941.
4. 4. Spellmeyer. D. C.; Houk, K. N. J. Org. Chem. 1987, 52, 959-974.
5. 5. Newcomb, M. Tetrahedron 1993, 49, 1151-1176.
6. 6. Beckwith, A. L. J. Tetrahedron 1981, 37, 3073-3100.
7. 7. Landolt-Bornstein. In New Series, Radical Reaction Rates in Liquids; Fischer, H., Ed.; Springer-Verlag: Berlin, 1984; Vol. 13, Parts a, b.
8. 8. Chambers, R. D. Fluorine in Organic Chemistry; John Wiley and Sons, Inc.: New York, 1973; pp. 173-179.
9. 9. Dolbier, W. R., Jr. Chem, Rev. 1996, in press.
10. 10. Feiring, A. E.; Logothetis, A. L. In Organofluorine Chemistry Principles and Commercial Applications; Banks, R. E.; Smart, B. E.; Tatlow, J. C. Eds.; Plenum Press: New York, 1994, pp. 339-396.
11. 11. Low, H. C.; Tedder, J. M.; Walton, J. C. J. Chem. Soc. Faraday Trans. 1976, 72, 1707-1714.
12. 12. Taken from the Ph. D. dissertation of Xiao X. Rong, University of Florida, 1995.
13. 5
14. C for substrates 1-5 are 4.24, 15.9, 12.9, 13.5 and 4.43, respectively.
15. 15. For further details as to experimental procedure see: Rong, X. X.; Pan, H.-Q.; Dolbier, W. R., Jr.; Smart, B. E. J. Am. Chem. Soc. 1994, 116, 4521-4522.
16. 19F NMR spectroscopy, and mass spectrometry.
17. 17. Dolbier, W. R., Jr.; Medinger, K. S. Tetrahedron 1982, 38, 2415-2419.
18. 18. Smart, B. E. In Molecular Structure and Energetics, Vol. 3: Studies of Organic Molecules; Liebman, J. F.; Greenberg, A., Eds.; VCH: New York, 1986.
19. 19. Paste, D. J.; Krasnansky, R.; Zercher, C. J. Org. Chem. 1987, 52, 3062-3072.
20. 20. Chiu, N. S.; Burrow, P. D.; Jordan, K. D. Chem. Phys. Lett. 1979, 68, 121-126.
21. 21. Fischer, H. In Substituent Effects in Radical Chemistry; Viehe, H. G., Janousek, Z., Merenyi, R., Eds.; Reidel: Dordrecht, 1986; pp 123-142.