Functionalization of saturated fluorocarbons with and without light

Journal of Fluorine Chemistry

Volumn 127, Issue 9, 2006, Pages 1158-1167

  Chen, Xudong ^a   Lemal, David M ^a  

^a Dartmouth College   (United States)

Author keywords

Diketonates; Enol ethers; Enolates; Fluorocarbon functionalization; Fluoropolymer modification; Ketyls; Photoreduction

Indexed keywords

EID: 33748290067     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2006.06.005     Document Type: Article

References (59)

1. In: Banks R.E., Smart B.E., and Tatlow J.C. (Eds). Organofluorine Chemistry, Principles and Commercial, Applications (1994), Plenum, New York
2. Lemal D.M. J. Org. Chem. 69 (2004) 1-11
3. Burdeniuc J., Chupka W., and Crabtree R.H. J. Am. Chem. Soc. 117 (1995) 10119-10120
4. Burdeniuc J., Jedlicka B., and Crabtree R.H. Chem. Ber./Recueil 130 (1997) 145-154
5. Saunders G. Angew. Int. Ed. 35 (1996) 2615-2617
6. Sung K., and Lagow R.J. J. Chem. Soc., Perkin Trans. I (1998) 637-638
7. Burdeniuc J., and Crabtree R.H. Science 271 (1996) 340-341
8. Kiplinger J.L., and Richmond T.G. J. Am. Chem. Soc. 118 (1996) 1805-1806
9. Kiplinger J.L., Richmond T.G., and Osterberg C.E. Chem. Rev. 94 (1994) 373-431
10. Gething B., Patrick C.R., Stacey M., and Tatlow J.C. Nature 183 (1959) 588-589
11. Marcella J.A., Gilicinski A.G., Coughlin A.M., and Pez G.P. J. Org. Chem. 57 (1992) 2856-2860
12. Burdeniuc J., and Crabtree R.H. J. Am. Chem. Soc. 118 (1996) 2525-2526
13. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Zakrzewski V.G., Montgomery Jr. J.A., Stratman R.E., Burant J.C., Dapprich S., Millam J.M., Daniels A.D., Kudin K.N., Strain M.C., Farkas O., Tomasi J., Barone V., Cossi M., Cammi R., Mennucci B., Pomelli C., Adamo C., Clifford S., Ochterski J., Petersson G.A., Ayala P.Y., Cui Q., Morokuma K., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Cioslowski J., Ortiz J.V., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Gomperts R., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Gonzalez C., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Andres J.L., Head-Gordon M., Replogle E.S., and Pople J.A. Gaussian '98 Revision A.5 (1998), Gaussian, Inc., Pittsburgh, PA
14. Burdeniuc J., and Crabtree R.H. Organometallics 17 (1998) 1582-1586
15. Kaprinidis N.A., and Turro N.J. Tetrahedron Lett. 37 (1996) 2373-2376
16. Stoyanov N.S., Ramchandani N., and Lemal D.M. Tetrahedron Lett. 40 (1999) 6549-6552
17. Fox M.F., and Hayon E. Trans. Faraday Soc. 1 72 (1976) 1990-1996
18. Blandamer M.J., and Fox M.F. Chem. Rev. 70 (1970) 59-93
19. Zhang Y., Smith J.R., and Lemal D.M. J. Am. Chem. Soc. 118 (1996) 9454-9455
20. X. Chen, D.M. Lemal, J. Fluorine Chem., in press.
21. Carter P.A., Patrick C.R., and Tatlow J.C. J. Fluorine Chem. 21 (1982) 407-411
22. Snegirev V.F., and Makarov K.N. Izv. Akad. Nauk SSSR, Ser. Khim. (1986) 1331-1340
23. For 17:. Meites L., and Zuman P. CRC Handbook Series in Organic Electrochemistry vol. 1 (1977), CRC Press, Cleveland, OH pp. 564-565
24. For 18:. Meites L., Zuman P., and Rupp E.B. CRC Handbook Series in Organic Electrochemistry vol. 3 (1977), CRC Press, Cleveland, OH pp. 306-307
25. For 19:. Meites L., and Zuman P. CRC Handbook Series in Organic Electrochemistry vol. 1 (1977), CRC Press, Cleveland, OH pp. 554-555
26. For 20:. Meites L., and Zuman P. CRC Handbook Series in Organic Electrochemistry vol. 1 (1977), CRC Press, Cleveland, OH pp. 684-685
27. For 21:. Meites L., and Zuman P. CRC Handbook Series in Organic Electrochemistry vol. 1 (1977), CRC Press, Cleveland, OH pp. 606-607
28. Hasegawa T., and Yamamoto H. Synlett (1999) 84-86
29. Chen X., and Lemal D.M. J. Org. Chem. 69 (2004) 8205-8208
30. Liebman J.F. J. Fluorine Chem. 3 (1973) 27-33
31. Martini T., and Schumann C. J. Fluorine Chem. 8 (1976) 535-540
32. Bekker R.A., Popkova V.Ya., and Knunyants I.L. Dokl. Akad. Nauk SSSR 229 (1976) 870
33. Bekker R.A., Popkova V.Ya., and Knunyants I.L. Dokl. Akad. Nauk SSSR, Engl. Transl. 229 (1976) 514
34. Lindner P.E., Correa R.A., Gino J., and Lemal D.M. J. Am. Chem. Soc. 118 (1996) 2556-2563
35. Yamada Y., Yamada T., Tasaka S., and Inagaki N. Macromolecules 29 (1996) 4331-4339
36. Badey J.P., Espuche E., Sage D., and Chabert B. Polymer 37 (1996) 1377-1386
37. Youxian D., Griesser H.J., Mau A., and Schmidt R. Polymer 32 (1991) 1126-1130
38. Rye R.R., and Arnold G.W. Langmuir 5 (1989) 1331-1334
39. Koh S.K., Park S.C., Kim S.R., Choi W.K., Jung H.J., and Pae K.D. J. Appl. Polym. Sci. 64 (1997) 1913-1921
40. Chang C.A., Baglin J.E., Schrott A.G., and Lin K.C. Appl. Phys. Lett. 51 (1987) 103-105
41. Chang C.A., Chan C.J., and Jones F. Appl. Phys. Lett. 59 (1991) 1069-1071
42. Girardeaux C., Idrissi Y., Pireaux J.J., and Caudano R. Appl. Surf. Sci. (1996) 586-590
43. Niino H., and Yabe A. Appl. Surf. Sci. (1996) 550-557
44. Heitz J., Niino H., and Yabe A. Appl. Phys. Lett. 68 (1996) 2648-2650
45. Allmer K., and Feiring A.E. Macromolecules 24 (1991) 5487-5488
46. Noh I., Chittur K., Goodman S.L., and Hubbell J.A. J. Polym. Sci. A 35 (1997) 1499-1514
47. Amatore C., Combellas C., Kanoufi F., Sella C., Thiebault A., and Thouin L. Chem. Eur. J. (2000) 820-835
48. Kavan L., Klima J., and Pserdlova M. Carbon 23 (1985) 45-49
49. Pelzbauer Z., Baldrian J., Jansta J., and Dousek F.P. Carbon 17 (1979) 317-322
50. Brace K.B., Combellas C., Dujardin E., Thiebault A., Delamar M., Kanoufi F., and Shanahan M. Polymer 38 (1997) 3295-3305
51. Chakrabarti N., and Jacobus J. Macromolecules 21 (1988) 3011-3014
52. Rye R.R. J. Polym. Sci. B, Polym. Phys. 26 (1988) 2133-2144
53. Sakurai H., Kubo Y., Shiotani M., Yahiro H., and Okuda Y. J. Appl. Polym. Sci. 74 (1999) 286-289
54. Costello C., and McCarthy T.J. Macromolecules 20 (1987) 2819-2828
55. Iqbal Z., Ivory D.M., Szobota J.S., Elsenbaumer R.L., and Baughman R.H. Macromolecules 19 (1986) 2992-2996
56. Costello C., and McCarthy T.J. Macromolecules 18 (1985) 2087-2088
57. Costello C., and McCarthy T.J. Macromolecules 17 (1984) 2940-2942
58. Schmiegel W.W. In: Hudlicky M., and Pavlath A.E. (Eds). Chemistry of Organic Fluorine Compounds vol. II (1995), American Chemical Society, Washington, DC pp.1101-1118
59. Croxtall B., Fawcett J., Hope E.G., and Stuart A.M. J. Fluorine Chem. 119 (2003) 65-73