First electronic investigation of the structure of alkenes compatible to carbon radicals bearing a single fluorine atom

Journal of Organic Chemistry

Volumn 61, Issue 1, 1996, Pages 301-303

  Takeuchi, Yoshio ^a   Kawahara, Shun Ichi ^a   Suzuki, Takanori ^a   Koizumi, Toru ^a   Shinoda, Hiroyuki ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0041955181     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951622j     Document Type: Article

References (22)

1. (a) Biomedicinal Aspects of Fluorine Chemistry; Filler, R., Kobayashi, Y., Eds.; Kodansha Ltd.: Tokyo, 1982.
2. (b) Biochemistry Involving Carbon-Fluorine Bonds; Filler, R., Ed.; American Chemical Society: Washington, DC, 1976.
3. (c) Fluorine in Bioorganic Chemistry; Welch, J T., Eswarakrishnan, S., Eds.; John Wiley & Sons: New York, 1991.
4. (d) Welch, J. T. Tetrahedron 1987, 43, 3123.
5. (e) Huang, H.-N.; Persico, D. F.; Lagow, R. J. J. Org. Chem. 1988, 53, 78.
6. (a) Takeuchi, Y.; Kanada, A.; Kawahara, S.; Koizumi, T. J. Org. Chem. 1993, 58, 3483.
7. (b) Takeuchi, Y.; Nagata, K.; Koizumi, T. J. Org Chem. 1987, 52, 5061.
8. Takeuchi, Y.; Nagata, K.; Koizumi, T. J. Org. Chem. 1989, 54, 5453.
9. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Giese, B , Ed.; Pergamon Press: Oxford, 1986; pp 4-35.
10. (a) Linderman, R. J.; Jamois, E. A. J. Fluorine Chem. 1991, 53, 79.
11. (b) Yamazaki, T. Chem. Times 1994, 154, 2.
12. (c) Ihara, M.; Kawabuchi, T.; Tokunaga, Y ; Fukumoto, K. Heterocycles 1995, 40, 97.
13. (d) Weinreb, C. K.; Hartsough, D.; Feldman, K. S. Tetrahedron Lett. 1995, 36, 6859.
14. Frish, M. J.; Trucks, G. W.; Head-Gordon, M.; Gill, P. M. W.; Wong, M. W.; Foresman, J. B.; Johnson, B. G.; Schlegel, H. B.; Robb, M. A.; Replogle, E. S.; Gomperts, R.; Andres, J. L.; Raghavachari, K.; Binkley, J. S.; Gonzalez, C.; Martin, R. L.; Fox, D. J.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Pople, J. A. Gaussian 92, Gaussian, Inc.; Pittsburgh, PA, 1992.
15. The energy level differences (by 6-31G) between the SOMO of the fluorinated radical 4b and the HOMO (or LUMO) of 6, 7, and 8 are 7.841 (5 538), 5.313 (5.891), and 6.758 (8.035) (eV), respectively. In the case of the simple radical 4a, however, the corresponding energy differences are 8.211 (5.168), 5.683 (5.521), and 7.128 (7.665) (eV), respectively.
16. Davis, A G.; Smith, P. J. In Comprehensive Organometallic Chemistry. The Synthesis, Reactions and Structures of Organometallic Compounds; Wilkinson, G., Stone, F. G. A., Abel, E. W , Eds.; Pergamon Press: Oxford, 1982; Vol 2, pp 519-627.
17. Even perfluorocarbon radicals have been the subject of few recent reports: (a) Avila, D. V.; Ingold, K. U.; Lusztyk, J.; Dolbier, W. R.; Pan, H.-Q. J. Am. Chem. Soc. 1993, 115, 1577. (b) Yoshida, M.; Morinaga, Y.; Iyoda, M. J. Fluorine Chem. 1994, 68, 33
18. Even perfluorocarbon radicals have been the subject of few recent reports: (a) Avila, D. V.; Ingold, K. U.; Lusztyk, J.; Dolbier, W. R.; Pan, H.-Q. J. Am. Chem. Soc. 1993, 115, 1577. (b) Yoshida, M.; Morinaga, Y.; Iyoda, M. J. Fluorine Chem. 1994, 68, 33
19. (a) Qian, C.-P.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 4602.
20. (b) Getty, S. J.; Hrovat, D. A.; Borden, W. T. J. Am. Chem. Soc. 1994, 116, 1521.
21. (c) Yamazaki, T.; Yamamoto, Y.; Kitazume, T J. Org. Chem. 1989, 54, 83.
22. (d) Welch, J. T.; Plummer, J. S.; Chou, T.-S. J. Org. Chem. 1991, 56, 353 and references therein