Experimental and theoretical studies on the reactivities of partially and fully fluorinated primary alkyl radicals

Tetrahedron

Volumn 53, Issue 29, 1997, Pages 9857-9880

  Bartberger, Michael D ^a   Dolbier Jr , William R ^a   Lusztyk, J ^b   Ingold, K U ^b  

^a University of Florida ^*  (United States)

^b NATIONAL RESEARCH COUNCIL CANADA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORINATED HYDROCARBON; ORGANOFLUORINE DERIVATIVE;

ARTICLE; CALCULATION; DRUG SYNTHESIS; ELECTRICITY; IN VITRO STUDY; PRESSURE; PRIORITY JOURNAL; QUANTUM CHEMISTRY; REACTION ANALYSIS; TEMPERATURE; THEORETICAL STUDY; THERMODYNAMICS;

EID: 0030739046     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00332-3     Document Type: Article

References (41)

1. (a) Avila, D. V.; Ingold, K. U.; Lusztyk, J.; Dolbier, W. R., Jr.; Pan, H.-Q. J. Am. Chem. Soc. 1993, 115, 1577-1579;
2. (b) Avila, D. V.; Ingold, K. U.; Lusztyk, J.; Dolbier, W. R., Jr.; Pan, H.-Q.; Muir, M. J. Am. Chem. Soc. 1995, 116, 99-104.
3. (a) Rong, X. X.; Pan, H.-Q.; Dolbier, W. R., Jr.; Smart, B. E. J. Am. Chem. Soc. 1994, 116, 4521-4522;
4. (b) Dolbier, W. R., Jr.; Rong, X. X. J. Fluorine Chem. 1994, 72, 235-240.
5. Avila, D. V.; Ingold, K. U.; Lusztyk, J.; Dolbier, W. R., Jr.; Pan, H.-Q. J. Org. Chem. 1996, 61, 2027-2030.
6. 2Ph, were isolated as pure compounds and fully characterized either from reaction mixtures by preparative GC or via alternative syntheses as described in the Experimental Section.
7. Kazanis, S.; Azarani, A.; Johnston, L. J. J. Phys. Chem. 1991, 95, 4430-4435.
8. 7
9. (a) Martell, J. M.; Boyd, R. J. J. Phys Chem. 1992, 96, 6287-6290;
10. (b) Martell, J. M.; Boyd, R. J.; Shi, Z. J. Phys. Chem. 1993, 97, 7208-7215.
11. th ed.; CRC Press: Boca Raton, 1995-96; 9-63-67.
12. Baldwin, R. R.; Drewery, G. R.; Walker, R. W. J. Chem. Soc. Faraday Trans. I 1984, 80, 2827-2835.
13. Rodgers, A. S.; Ford, W. G. F. Int. J. Chem. Kinet. 1973, 5, 965-975.
14. Seakins, P. W.; Pilling, M. J.; Niiranen, J. T.; Gutman, D.; Krasnoperov, L. N. J. Phys. Chem. 1992, 96, 9847-9855.
15. Pickard, J. M.; Rodgers, A. S. J. Am. Chem. Soc. 1977, 99, 691-694.
16. Wu, E. C.; Rodgers, A. S. J. Phys. Chem. 1974, 78, 2315-2317.
17. Evans, B. S.; Whittle, E. Int. J. Chem. Kinet. 1981, 13, 59-63.
18. Singh, U. C.; Kollman, P. A. J. Comp. Chem. 1984, 5, 129.
19. Besler, B. H.; Merz, K. M., Jr.; Kollman, P. A. J. Comp. Chem. 1990, 11, 431.
20. Dolbier, W. R., Jr.; Bartberger, M. D. Unpublished results.
21. See footnotes 10 and 11 in Ref. 3.
22. 20
23. Chatgilialoglu, C. Accts. Chem. Res. 1992, 25, 188-194.
24. McMillen, D. F.; Golden, D. M. Annu. Rev. Phys. Chem. 1982, 33, 493-532, and references cited therein.
25. Bordwell, F. G.; Zhang, X.-M. Acc. Chem. Res. 1993, 26, 510-517, and references cited therein.
26. Pasto, D. J. J. Am. Chem. Soc. 1988, 110, 8164-8175.
27. Bernardi, F.; Cherry, W.; Shaik, S.; Epiotis, N. D. J. Am. Chem. Soc. 1978, 100, 1352-1356.
28. Luo, Y.-R.; Benson, S. W. Accts. Chem. Res. 1992, 25, 375-381.
29. Wiberg, K. B.; Rablen, P. R. J. Am. Chem. Soc. 1993, 115, 614-625.
30. Heats of formation were taken from the NIST Standard Reference Database 25. NIST Structures Properties Database and Estimation Program 1991; U.S. Department of Commerce: Gaithersburg, MD 20899, 1991.
31. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
32. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L., Fox, D. J., Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, Revision C.3, Gaussian, Inc., Pittsburgh PA, 1995.
33. Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502-16513; Bauschlicher, C. W., Jr.; Partridge, H. J. Chem. Phys. 1995, 103, 1788-1791.
34. Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502-16513; Bauschlicher, C. W., Jr.; Partridge, H. J. Chem. Phys. 1995, 103, 1788-1791.
35. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986.
36. 2 torsion.
37. Gonzalez, J.; Foti, C. J.; Elsheimer, S. J. Org. Chem. 1991, 56, 4322-4325.
38. Burton, D. J.; Kehoe, L. J. J. Org. Chem. 1970, 35, 1339-1342.
39. Zav'yalov, S. I.; Ezhova, G. I.; Sitkareva, I. V.; Dorofeeva, O. V.; Zavozin, A. G.; Rumyantseva, E. E. Izv. Akad. Nauk. SSSR, 1989, 10, 2392-2393.
40. Rondestvedt, C. S., Jr. J. Org. Chem. 1977, 42, 1985-1990.
41. Takeyama, Y.; Ichinose, Y.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1989, 30, 3159-3162.