Cyclization reactivities of fluorinated hex-5-enyl radicals

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 2, 1998, Pages 219-231

  Dolbier Jr , William R ^a   Rong, Xiao X ^a   Bartberger, Michael D ^a   Koroniak, Henryk ^a   Smart, Bruce E ^b   Yang, Zhen Yu ^b  

^a University of Florida ^*  (United States)

^b DUPONT COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000404542     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (68)

1. A. L. J. Beckwith and S. A. Glover, Aust. J. Chem., 1987, 40, 157.
2. A. L. J. Beckwith and C. H. Schiesser, Tetrahedron, 1985, 41, 3925.
3. M. Newcomb, J. H. Homer, M. A. Filipkowski, C. Ha and S.-U. Park, J. Am. Chem. Soc., 1995, 117, 3674.
4. M. Newcomb, M. A. Filipkowski and C. C. Johnson, Tetrahedron Lett., 1995, 36, 3643.
5. M. Newcomb, Tetrahedron, 1993, 49, 1151 and references therein.
6. J. M. Tedder, Angew. Chem., Int. Ed. Engl., 1982, 21, 401.
7. B. Giese, Angew. Chem., Int. Ed. Engl., 1983, 22, 753.
8. D. C. Spellmeyer and K. N. Houk, J. Org. Chem., 1987, 52, 959.
9. D. V. Avila, K. U. Ingold, J. Lusztyk, W. R. Dolbier, Jr. and H.-Q. Pan, J. Am. Chem. Soc., 1993, 115, 1577.
10. D. V. Avila, K. U. Ingold, J. Lusztyk, W. R. Dolbier, Jr., H.-Q. Pan and M. Muir, J. Am. Chem. Soc., 1994, 116, 99.
11. D. V. Avila, K. U. Ingold, J. Lusztyk, W. R. Dolbier, Jr. and H.-Q. Pan, J. Org. Chem., 1996, 61, 2027.
12. W. R. Dolbier, Jr., Chem. Rev., 1996, 96, 1557.
13. B. E. Smart, A. E. Feiring, C. G. Krespan, Z.-Y. Yang, M.-H. Hung, P. R. Resnick, W. R. Dolbier, Jr. and X. X. Rong, Macromol. Symp., 1995, 98, 753; M.-H. Hung, P. R. Resnick, B. E. Smart and W. H. Buck, in Polymeric Materials Encyclopedia, ed. J. C. Salamone, CRC Press, Boca Raton, 1996, vol. 4, pp. 2466-2476.
14. B. E. Smart, A. E. Feiring, C. G. Krespan, Z.-Y. Yang, M.-H. Hung, P. R. Resnick, W. R. Dolbier, Jr. and X. X. Rong, Macromol. Symp., 1995, 98, 753; M.-H. Hung, P. R. Resnick, B. E. Smart and W. H. Buck, in Polymeric Materials Encyclopedia, ed. J. C. Salamone, CRC Press, Boca Raton, 1996, vol. 4, pp. 2466-2476.
15. X. X. Rong, H.-Q. Pan, W. R. Dolbier, Jr., and B. E. Smart, J. Am. Chem. Soc., 1994, 116, 4521.
16. W. R. Dolbier, Jr. and X. X. Rong, Tetrahedron Lett., 1996, 37, 5321.
17. W. R. Dolbier, Jr. and X X. Rong, J. Fluorine Chem., 1995, 72, 235.
18. M. D. Bartberger, W. R. Dolbier, Jr., J. Lusztyk and K. U. Ingold, Tetrahedron, 1997, 53, 9857.
19. W. R. Dolbier, Jr., X. X. Rong, B. E. Smart and Z.-Y. Yang, J. Org. Chem., 1996, 61, 4824.
20. H. C. Low, J. M. Tedder and J. C. Walton, J. Chem. Soc., Faraday Trans., 1976, 72, 1707.
21. A. L. J. Beckwith, Tetrahedron, 1981, 37, 3073.
22. B. E. Smart, in Molecular Structure and Energetics, Vol. 3: Studies of Organic Molecules, ed. J. F. Liebman and A. Greenberg, VCH, New York, 1986.
23. N. S. Chiu, P. D. Burrow and K. D. Jordan, Chem. Phys. Lett., 1979, 68, 121.
24. H. Fischer, in Substituent Effects in Radical Chemistry, ed. H. G. Viehe, Z. Janousek and R. Merenyi, Reidel, Dordrecht, 1986, pp. 123-142.
25. W. R. Dolbier, Jr. and K. S. Medinger, Tetrahedron, 1982, 38, 2415.
26. D. J. Pasto, R. Krasnansky and C. Zercher, J. Org. Chem., 1987, 52, 3062.
27. T. Zytowski and H. Fischer, J. Am. Chem. Soc., 1996, 118, 437.
28. A. L. J. Beckwith, I. A. Blair and G. Phillipou, Tetrahedron Lett., 1974, 2251; see also M. Newcomb, N. Tanaka, A. Bouvier, C. Tronche, J. H. Horner, O. M. Musa and F. N. Martinez, J. Am. Chem. Soc., 1996, 118, 8505.
29. A. L. J. Beckwith, I. A. Blair and G. Phillipou, Tetrahedron Lett., 1974, 2251; see also M. Newcomb, N. Tanaka, A. Bouvier, C. Tronche, J. H. Horner, O. M. Musa and F. N. Martinez, J. Am. Chem. Soc., 1996, 118, 8505.
30. 29 would seem to imply that their configurations are very similar and that they are distinctly pyramidal.
31. H. Fischer, in Magnetic Properties of Free Radicals, Landolt-Bornstein, New Series, ed. H. Fischer and K.-H. Hellwege, Springer-Verlag, Berlin, 1977, vol. 9, ch. 3.
32. 32
33. V. Madhaven, R. H. Schuler and R. W. Fessenden, J. Am. Chem. Soc., 1978, 100, 888.
34. B. C. Gilbert, J. R. Lindsay Smith, E. C. Milne, A. C. Whitwood and P. Taylor, J. Chem. Soc., Perkin Trans. 2, 1993, 2025.
35. M. W. Wong, A. Pross and L. Radom, J. Am. Chem. Soc., 1994, 116, 6284; M. W. Wong, A. Pross and L. Radom, J. Am. Chem. Soc., 1994, 116, 11 938. For an earlier study, see: M. J. S. Dewar and S. Olivella, J. Am. Chem. Soc., 1978, 100, 5290.
36. M. W. Wong, A. Pross and L. Radom, J. Am. Chem. Soc., 1994, 116, 6284; M. W. Wong, A. Pross and L. Radom, J. Am. Chem. Soc., 1994, 116, 11 938. For an earlier study, see: M. J. S. Dewar and S. Olivella, J. Am. Chem. Soc., 1978, 100, 5290.
37. M. W. Wong, A. Pross and L. Radom, J. Am. Chem. Soc., 1994, 116, 6284; M. W. Wong, A. Pross and L. Radom, J. Am. Chem. Soc., 1994, 116, 11 938. For an earlier study, see: M. J. S. Dewar and S. Olivella, J. Am. Chem. Soc., 1978, 100, 5290.
38. CRC Handbook of Chemistry and Physics, ed. D. R. Lide, CRC Press, Boca Raton, 76th edn., 1995-1996, pp. 63-67.
39. R. R. Baldwin, G. R. Drewery and R. W. Walker, J. Chem. Soc., Faraday Trans. 1, 1984, 80, 2827.
40. A. S. Rodgers and W. G. F. Ford, Int. J. Chem. Kinet., 1973, 5, 965.
41. 29
42. T. J. Buckley and R. D. Johnson, III from poster presentation at 14th Winter Fluorine Conference, St. Petersburg, FL, January, 1997.
43. NIST Standard Reference Database 25. NIST Structures Properties Database and Estimation Program 1991; US Department of Commerce: Gaithersburg. MD 20899, 1991.
44. A. A. Christodoulides, D. L. McCorkle and L. G. Christophorou, in Electron-Molecule Interactions and their Applications, ed. L. G. Christophorou, Academic Press, Orlando, 1984, vol. 2, pp. 423-641.
45. B. Delest, H.-Q. Pan and W. R. Dolbier, Jr., unpublished results, see ref. 12.
46. The endo products were demonstrated to be formed under kinetic control, by control experiments which included the generation of the respective cyclopentylmethyl radicals under concentration conditions identical to those used in the competition studies, with no consequent cyclohexyl products being observed.
47. Ab initio calculations (UHF/4-31G*): M. D. Bartberger and W. R. Dolbier, Jr., unpublished results.
48. B. E. Smart and Z.-Y. Yang, USP 5 557 018/1996.
49. The model hex-5-enyl radical cyclizations all involve primary radicals whereas the corresponding radicals involved in the diene polymerizations are all secondary, so both the rates and regiochemistry could differ significantly; see G. B. Butler, Cyclopolymerization and Cyclocopolymerization, Marcel Dekker, New York, 1992.
50. J. Homer and L. F. Thomas, Trans. Faraday Soc., 1963, 59, 2431; A. Peake and L. F. Thomas. Trans. Faraday Soc., 1966, 62, 2980.
51. J. Homer and L. F. Thomas, Trans. Faraday Soc., 1963, 59, 2431; A. Peake and L. F. Thomas. Trans. Faraday Soc., 1966, 62, 2980.
52. J. Merritt, J. Org. Chem., 1966, 31, 1859.
53. 44 Both polymers, however, are intractable and have eluded unambiguous structural characterization.
54. D. Y. Chi, D. O. Kiesewetter, J. A. Katzenellenbogen, M. R. Kilbourn and M. J. Welch, J. Fluorine Chem., 1986, 31, 99.
55. H. C. Brown, C. G. Rao and S. U. Kuikarni, Synthesis, 1979, 704.
56. D. G. Cox, N. Gurusamy and D. J. Burton, J. Am. Chem. Soc., 1985, 107, 2811.
57. D. G. Naae and D. J. Burton, Synth. Commun., 1973, 3, 197.
58. M. R. Detty, Tetrahedron Lett., 1979, 20, 4189.
59. E. J. Corey and A. Venkateswarlu, J. Am. Chem. Soc., 1972, 94, 6190.
60. W. F. Bailey and E. R. Punzalan, J. Org. Chem., 1990, 55, 5404.
61. J.-F. Normant, J. Organomet. Chem., 1990, 400, 19.
62. T. Dubuffet, R. Sauvetre and J.-F. Normant, J. Organomet. Chem., 1988, 341, 11.
63. J. P. Gillet, R. Sauvetre and J.-F. Normant, Synthesis, 1986, 355.
64. J. H. Babler and K. P. Spina, Synth. Commun., 1984, 14, 1313.
65. E. J. Corey and W. Su, Tetrahedron Lett., 1984, 25, 5119.
66. C. G. Krespan, J. Org. Chem., 1958, 23, 2016.
67. Synthesis of Fluoroorganic Compounds, ed. IL. Knunyants and G. G. Yakobson, Springer-Verlag, New York, 1985, pp. 16-17; M. Hauptschein, M. Braid and A. Fainberg, J. Am. Chem. Soc., 1961, 83, 2495.
68. Synthesis of Fluoroorganic Compounds, ed. IL. Knunyants and G. G. Yakobson, Springer-Verlag, New York, 1985, pp. 16-17; M. Hauptschein, M. Braid and A. Fainberg, J. Am. Chem. Soc., 1961, 83, 2495.