Synthesis of γ-(Electron-withdrawing group)-Substituted a,a-Difluoro Ketones by UV-Initiated Addition of Iododifluoromethyl Ketones with Electron-Deficient Alkenes

Journal of Organic Chemistry

Volumn 60, Issue 21, 1995, Pages 6798-6805

  Qiu, Zai Ming ^a   Burton, Donald J ^a  

^a UNIVERSITY OF IOWA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0348172958     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00126a032     Document Type: Article

References (73)

1. Filler, R. Biochemistry Involving Carbon-Fluorine Bonds; American Chemical Society: Washington, DC, 1976.
2. Banks, R. E. Organofluorine Chemicals and their Industrial Applications; Ellis Hor-wood: Chichester, 1979.
3. Filler, R.; Kobayashi, Y. Biochemical Aspects of Fluorine Chemistry; Elservier Biomedical Press and Kodan-sha Ltd.: New York, 1982.
4. Liebman, J. F.; Greenberg, A.; Dolbier, W. R. Fluorine-Containing Molecules: Structure, Reactivity, Synthesis and Applications; VCH Publisherers: New York, 1988; Chapter 11.
5. Welch, J. T. Selective Fluorination in Organic and Bioorganic Chemistry; American Chemical Society, Washington, DC, 1991.
6. Thaisrivongs, S.; Pals, D. T.; Kati, W. M.; Turner, S. R.; Thomasco, L. M. J. Med. Chem. 1985, 28, 1553.
7. Welch, J. T. Tetrahedron 1987, 43, 3123.
8. Dreyer, G. B.; Metealf, B. W. Tetrahedron Lett. 1988, 29, 6885.
9. Takahashi, L. H.; Radhakrishnan, R.; Rosenfield, R. E., Jr.; Meyer, E. F., Jr.; Trainor, D. A. J. Am. Chem. Soc. 1989, 111, 3368.
10. Sham, H. L.; Wideburg, N. E.; Spanton, S. G.; Kohlbrennet, W. E.; Betebenner, D. A.; Kempf, D. J.; Norbeck, D. W.; Plattner, J. J.; Erickson, J. W. J. Chem. Soc, Chem. Commun. 1991, 110.
11. Gelb, M. H.; Svaren, J. P.; Abeles, R. H. Biochemistry 1985, 24, 1813.
12. Imperiala, B.; Abeles, R. H. Biochemistry 1986, 25, 151.
13. Yuan, W.; Berman, R. J.; Gelb, M. H. J. Am. Chem. Soc. 1987, 109, 8071.
14. Jauhiainen, M.; Yuan, W.; Gelb, M. H.; Dolphin, P. J. J. Biol. Chem. 1989, 264, 1963.
15. Takahashi, L. H.; Radhakrishnan, R.; Rosenfield, R. E., Jr.; Meyer, E. F., Jr.; Trainor, D. A. J. Am. Chem. Soc. 1989, 111, 3368.
16. Sham, H. L.; Wideburg, N. E.; Spanton, S. G.; Kohlbrenner, W. E.; Betebenner, D. A.; Kempf, D. J.; Norbeck, D. W.; Plattner, J. J.; Erickson, J. W. J. Chem. Soc., Chem. Commun. 1991, 110.
17. Parisi, M. F.; Abeles, R. H. Biochemistry 1992, 31, 9429.
18. Quinn, D. M.; Lin, G. H. U. S. Patent 5,093,371, 1992;
19. Chem. Abstr. 1992, 116, 221582g.
20. Mehdi, S. Bioorg. Chem. 1993, 21, 249.
21. Schirlin, D.; Baltzer, S.; Van Dorsselaer, V.; Weber, F.; Weill, C.; Altenburger, J. M.; Neises, B.; Flynn, G.; Remy, J. M.; Tarnus, C. Bioorg. Med. Chem. Lett. 1993, 3, 253.
22. Edwards, P. N. In Organofluorine Chemistry, Principles and Commercial Applications; Bank, R. E., Smart, B. E., Tatlow, Eds.; Plenum Press: New York, 1994; Chaper 24, p 525.
23. Hallinan, E. A.; Fried, J. Tetrahedron Lett. 1984, 25, 2301.
24. Kitagawa, O.; Taguchi, T.; Kobayashi, Y. Tetrahedron Lett. 1988, 29, 1803.
25. B.O. Kitagawa; Kobayashi, Y.; Taguchi, T. Chem. Lett. 1990, 1307.
26. Kuroboshi, M.; Ishihara, T. Tetrahedron Lett. 1987, 28, 6481.
27. Yang, Z. Y.; Burton, D. J. J. Fluorine Chem. 1989, 4, 339.
28. Yang, Z. Y.; Burton, D. J. J. Org. Chem. 1991, 56, 1037.
29. Ishihara, T.; Miwatashi, S.; Kuroboshi, M.; Utimoto, K. Tetrahedron Lett. 1991, 32, 1069.
30. Hanzawa, Y.; Inazawa, K.; Kon, A.; Aoki, H.; Kobayashi, Y. Tetrahedron Lett. 1987, 28, 659.
31. Sham, H. L.; Betebenner, D. A. J. Chem. Soc, Chem. Commun. 1991, 1134.
32. Kurabeshi, M.; Ishihara, T. Bull. Chem. Soc. Jpn. 1990, 63, 428.
33. Lang, R. W.; Schaub, B. Tetrahedron Lett. 1988, 29, 2943.
34. Kitagawa, O.; Taguchi, T.; Kobayashi, Y. Tetrahedron Lett. 1988, 29, 1803.
35. Taguchi, T.; Kitagawa, O.; Suda, Y.; Ohkawa, S.; Hashimoto, A.; Itaka, Y.; Kobayashi, Y. Tetrahedron Lett. 1988, 29, 5291.
36. Kitagawa, O.; Hashimoto, A.; Taguchi, T. Chem. Lett. 1990, 1307.
37. Rozen, S.; Filler, R. Tetrahedron 1985, 41, 1111 and references cited therein.
38. Xu, Z. Q.; DesMarteau, D. D.; Gotoh, Y. J. Fluorine Chem. 1992, 58, 71 and references therein,
39. Resnati, G.; DesMarteau, D. D. J. Org. Chem. 1991, 56, 4925; 1992, 57, 4281.
40. Differding, E.; Ruegg, G. M.; Lang, R. W. Tetrahedron Lett. 1991, 32, 1779.
41. Seyferth, D.; Simon, R. M.; Sepelak, D. J.; Klein, H. A. J. Am. Chem. Soc. 1983, 105, 4634.
42. Zupan, M.; Iskra, J.; Stavber, S. J. Org. Chem. 1995, 60, 259.
43. Hudlicky, M. Chemistry of Fluorine Compounds, 2nd ed.; Ellis Harwood: Chichester, 1976.
44. Chambers, R. D. Fluorine in Organic Chemistry; Willey-Interscience: New York, 1973.
45. Sheppard, W. A.; Sharts, C. M. Organic Fluorine Chemistry; W. A. Benjamin, Inc.: New York, 1969.
46. Burton, D. J.; Kehoe, L. J. J. Org. Chem. 1970, 35, 1339.
47. Feiring, A. E. J. Org. Chem. 1985, 50, 3269.
48. Brace, N. O. J. Org. Chem. 1979, 44, 1964.
49. Andrieux, C. P.; Gelis, L.; Medebielle, M.; Pinson, J.; Saveant, J. M. J. Am. Chem. Soc. 1990, 112, 3509 and references cited therein,
50. Hu, C. M.; Chen, J. Tetrahedron Lett., 1993, 34, 5975.
51. Beckwith, A. L. J.; Easton, C. J.; Lawrence, T.; Serelis, A. K. Aust. J. Chem. 1983, 36, 545.
52. Chen, Q. Y.; Qiu, Z. M. J. Fluorine Chem. 1986, 31, 301; 1986, 35, 343.
53. Chen, Q. Y.; Qiu, Z. M.; Yang, Z. Y. J. Fluorine Chem. 1987, 36, 149.
54. Chen, Q. Y.; Yang, Z. Y.; Qiu, Z. M. Kexue Tongbao 1987, 183, 593.
55. Yang, Z. Y.; Burton, D. J. J. Org. Chem. 1991, 56, 5125; 1992, 57, 5144.
56. Burton, D. J.; Thenappan, A.; Yang, Z. Y. In Selective Fluorination in Organic and Bioorganic Chemistry; Welch, J. T., Ed.; ACS Symposium Series, 456; American Chemical Society: Washington, DC, Chapter 7, pp 91-104.
57. Yang, Z. Y.; Burton, D. J. J. Org. Chem. 1992, 57, 4676.
58. Su, D. B.; Zhu, R. X.; Qiu, Z. M.; Chen, Q. Y. Acta. Chim. Sin. 1990, 48, 596.
59. Yang, Z. Y.; Nguyen, B. V.; Burton, D. J. Synlett 1992, 141.
60. Haszeldine, R. N. J. Chem. Soc. 1950, 3037; 1949, 2856.
61. Haszeldine, R. N. J. Chem. Soc. 1952, 3490.
62. Haszeldine, R. N.; Steele, B. R. J. Chem. Soc. 1953, 1199.
63. Brace, N. O. J. Org. Chem. 1964, 29, 1247.
64. Brace, N. O. J. Org. Chem. 1962, 27, 4491; 1962, 27, 3033.
65. Chen, Q. Y.; Yang, Z. Y. J. Fluorine Chem. 1985, 28, 399.
66. Qiu, Z. M.; Burton, D. J. Tetrahedron Lett. 1993, 34, 3239.
67. Qiu, Z. M.; Burton, D. J. The University of Iowa, unpublished results.
68. Qiu, Z. M.; Burton, D. J. Tetrahedron Lett. 1994, 35, 1813;
69. J. Org. Chem. to be published.
70. Qiu, Z. M.; Burton, D. J. Tetrahedron Lett. 1994, 35, 4319.
71. Qiu, Z. M.; Burton, D. J. A New Precursor for the Synthesis of β-Fluoropyrroles, α,α.-Difluoro-y-iodotrimethylketones; Presented in part at the 12th Winter Fluorine Conference, Jan 1995, St. Petersburg, FL; Abstr. No. 35.
72. Chen, Q. Y.; Yang, Z. Y.; Zhao, C. X.; Qiu, Z. M. J. Chem. Soc, Perkin Trans 1 1988, 563 and references cited therein.
73. Qiu, Z. M.; Burton, D. J. J. Org. Chem. 1995, 60, 3465.