Radical addition reactions of fluorinated species. Part 7. Highly selective two-step synthesis of 1-(polyfluoroalkyl)ethane-1,2-diols; Regioselectivity of the additions of methylated 1,3-dioxolanes to perfluoroolefins

Journal of Fluorine Chemistry

Volumn 94, Issue 2, 1999, Pages 141-156

  Církva, Vladimír ^a   Paleta, Oldrich ^a  

^a INSTITUTE OF CHEMICAL TECHNOLOGY   (Czech Republic)

Author keywords

1 (Poly fluoroalkyl)ethane 1,2 diyl bis methacrylates; 1 (Polyfluoroalkyl)ethane 1,2 diols; Fluoroolefins; Hydrolysis of fluoroalkylated 1,3 dioxolanes; Photo addition; Radical stability; Regioselective radical addition; Steric effects

Indexed keywords

EID: 0042957252     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-1139(98)00356-X     Document Type: Article

References (71)

1. Paleta O., Církva V., Budková Z., Böhm S. J. Fluorine Chem. 86:1997;155.
2. Boutevin B., Robin J.J. Adv. Polym. Sci. 102:1992;105.
3. Trischler F.D., Hollander J. Jr. J. Polym. Sci., Part A-1, Polym. Chem. 7:1969;971.
4. Johncock P., Barnett S.P., Rickard P.A. J. Polym. Sci., Part A-1, Polym. Chem. 24:1969;971.
5. Mera A.E., Griffith J.R. J. Fluorine Chem. 69:1994;151.
6. R.A. Mitsch, J.L. Zollinger, US Patent 3 972 856 (1976).
7. R.A. Mitsch, J.L. Zollinger, Ger. Offen. 2 011 774 (1970).
8. Mitsch R.A., Zollinger J.L. Chem. Abs. 74:1971;13999.
9. Orear J.G., Griffith J.R., Reines S.A. J. Paint. Technol. 552:1971;873.
10. Hollander J. Jr., Trischler F.D. J. Am. Chem. Soc., Div. Polym. Chem. 8:1967;491.
11. M.F. Refojo, in: M. Ruben, M. Guillon (Eds.), Contact Lens Practise, Chapter 2, Chapman and Hall, London, 1994.
12. F. Yamamoto, T. Suzuki, M. Ikari, S. Saito, A. Ohmori, T. Yasuhara, Eur. Patent Appl. EP 213 412 (1987).
13. Yamamoto F., Suzuki T., Ikari M., Saito S., Ohmori A., Yasuhara T. Chem. Abs. 108:1988;26994.
14. T. Hogi, N. Osawa, Jpn. Kokai Tokkyo Koho JP 0 497 117 (1992).
15. Hogi T., Osawa N. Chem. Abs. 117:1992;118550.
16. Park J.D., Rogers F.E., Lacher J.R. J. Org. Chem. 26:1961;2089.
17. K. von Werner, Ger. Offen. DE 3 525 494 (1987).
18. von Werner K. Chem. Abs. 106:1987;155891.
19. M. Yoshizumi, A. Nakamura, Y. Yamashita, K. Kaneko, Jpn. Kokai Tokkyo Koho JP 1 305 045 (1989).
20. Yoshizumi M., Nakamura A., Yamashita Y., Kaneko K. Chem. Abs. 112:1990;197619.
21. Y. Animoto, S. Daimon, M. Okamoto, Jpn. Patent 7 884 909 (1978).
22. Animoto Y., Daimon S., Okamoto M. Chem. Abs. 89:1978;214891.
23. Herrmann W.A., Eder S.J., Scherer W. Angew. Chem. 104:1992;1371.
24. Herrmann W.A., Eder S.J. Chem. Ber. 126:1993;31.
25. McBee E.T., Burton T.M. J. Am. Chem. Soc. 74:1952;3022.
26. Rausch D.A., Lovelace A.M., Coleman L.E. J. Org. Chem. 21:1956;1328.
27. Ramachandran P.V., Gong B., Brown H.C. J. Org. Chem. 60:1995;41.
28. Kubota T., Shirakura H., Tanaka T. J. Fluorine Chem. 54:1991;286.
29. Ayari A., Szönyi S., Rouvier E., Cambon A. J. Fluorine Chem. 50:1990;67.
30. M. Tanaka, J. Agou, M. Kuwahara, J. Sakashita, T. Shimoda, M. Sudou, Eur. Patent Appl. EP297 822 (1989).
31. Tanaka M., Agou J., Kuwahara M., Sakashita J., Shimoda T., Sudou M. Chem. Abs. 111:1989;135008.
32. B. Maillard, M. Cazaux, R. Lalande, Bull. Soc. Chim. Fr. (1971) 467.
33. B. Maillard, M. Cazaux, R. Lalande, Bull. Soc. Chim. Fr. (1973) 1368.
34. Dědek V., Hemer I. Collect. Czech. Chem. Commun. 50:1985;2743.
35. O. Paleta, V. Církva, J. Kvíčala, Czech. Patent 282 756 (1997).
36. Paleta O., Budková Z., Kvíčala J., Timpe H.J. Collect. Czech. Chem. Commun. 60:1995;636.
37. A. Gilbert, J. Baggot, Essentials of Molecular Photochemistry, Blackwell, London, 1991, p. 168 and 229.
38. Kvíčala J., Dolenský B., Paleta O. J. Fluorine Chem. 85:1997;117.
39. Paleta O., Štěpán L., Danda A., Kvíčala J., Dědek V. J. Fluorine Chem. 45:1989;331.
40. Ayari A., Szönyi S., Rouvier E., Cambon A. Bull. Soc. Chim. Fr. 129:1992;315.
41. Ishihara K., Kurihara H., Yamamoto H. J. Org. Chem. 58:1993;3791.
42. Cohen T., Dughi M., Notaro V.A., Pinkus G. J. Org. Chem. 27:1962;814.
43. Hirano M., Morimoto T. J. Chem. Soc., Perkin Trans. 2:1984;1033.
44. Sauty L.J., Azer S., McClelland R.A. J. Am. Chem. Soc. 110:1988;2909.
45. McClelland R.A., Seaman N.E., Cramm D. J. Am. Chem. Soc. 106:1984;4511.
46. Tedder J.M., Walton J.C. Acc. Chem. Res. 9:1976;183.
47. Giese B. Angew. Chem., Int. Ed. Engl. 16:1977;125.
48. Giese B. Angew. Chem., Int. Ed. Engl. 22:1983;753.
49. Tedder J.M., Walton J.C. Tetrahedron. 36:1980;701.
50. Tedder J.M., Walton J.C. Tetrahedron. 38:1982;313.
51. Tedder J.M. Angew. Chem. 94:1982;433.
52. Tedder J.M. Angew. Chem., Int. Ed. Engl. 22:1982;401.
53. Walling C. Tetrahedron. 41:1985;3887.
54. B. Giese, in: M. Regitz, B. Giese (Eds.), Methoden der Organischen Chemie (Houben-Weyl), vol. E19a, Part 1, Thieme, Stuttgart, 1989, p. 1.
55. Abroskina T.N., Sorokin A.D., Kudryavcev R.V., Cheburkov I.A. Izv. Akad. Nauk. USSR, Ser. Khim. 23:1974;1823.
56. Courtieu J., Jullien J., Lai N.T., Gonord P., Kan S.K. Tetrahedron. 32:1976;669.
57. Dmowski W., Voelbnagel-Neugebauer H. J. Fluorine Chem. 81:1981;223.
58. Chambers R.D., Grievson B. J. Chem. Soc., Perkin Trans. 1:1985;2215.
59. Šendrik V.P., Paleta O., Dědek V. Collect. Czech. Chem. Commun. 39:1974;1061.
60. Šendrik V.P., Paleta O., Dědek V. Collect. Czech. Chem. Commun. 42:1977;2530.
61. D.C. Nonhebel, J.C. Walton, Free-Radical Chemistry, Chapter 8, Cambridge University Press, Cambridge, 1974.
62. Paleta O., Církva V., Kvíčala J. J. Fluorine Chem. 80:1996;125.
63. Církva V., Polák R., Paleta O. J. Fluorine Chem. 80:1996;135.
64. O. Paleta, V. Dědek, S. Neuenfeld, H.-J. Timpe, Czech. Patent 268 247 (1989).
65. Paleta O., Dědek V., Neuenfeld S., Timpe H.-J. Chem. Abs. 114:1991;206556.
66. Haszeldine R.N., Rowland R., Sheppard R.P., Tipping A.E. J. Fluorine Chem. 28:1985;291.
67. LaZerte J.D., Koshar R.J. J. Am. Chem. Soc. 77:1955;910.
68. Bordwell F.G., Zhang X.-M., Alnajjar M.S. J. Am. Chem. Soc. 114:1992;7623.
69. Dauben J., Löken B. J. Am. Chem. Soc. 76:1954;1362.
70. B.S. Furniss, A.J. Hammford, P.W.G. Smith, A.R. Tatchell, Vogel's Textbook of Practical Organic Chemistry, 5th ed., Chapter 6, Wiley, New York, 1991.
71. Kvíčala J., Paleta O., Dědek V. J. Fluorine Chem. 47:1990;441.