[p-((trifluorovinyl)oxy)phenyl]lithium: Formation, synthetic utility, and theoretical support for a versatile new reagent in fluoropolymer chemistry

Organometallics

Volumn 17, Issue 5, 1998, Pages 783-785

  Ji, Junmin ^a   Narayan Sarathy, Sridevi ^a   Neilson, Robert H ^a   Oxley, James D ^a   Babb, David A ^b   Rondan, Nelson G ^b   Smith Jr , Dennis W ^b  

^a TEXAS CHRISTIAN UNIVERSITY   (United States)

^b DOW CHEMICAL COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000817532     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9710531     Document Type: Article

References (33)

1. See for example: (a) Hudlicky, M. Chemistry of Organic Fluorine Compounds, 2nd ed.; Ellis Horwood: Chichester, England, 1976; pp 285-290, 407-410. (b) Chambers, R. D. Fluorine in Organic Chemistry; Wiley: New York, 1973; pp 2-3, 148-170. (c) Chambers, R. D.; Mobbs, R. H. Adv. Fluorine Chem. 1965, 4, 50. (d) Miller, W. T.; Fried, J. H.; Godwhite, H. J. Am. Chem. Soc. 1960, 82, 3091.
2. See for example: (a) Hudlicky, M. Chemistry of Organic Fluorine Compounds, 2nd ed.; Ellis Horwood: Chichester, England, 1976; pp 285-290, 407-410. (b) Chambers, R. D. Fluorine in Organic Chemistry; Wiley: New York, 1973; pp 2-3, 148-170. (c) Chambers, R. D.; Mobbs, R. H. Adv. Fluorine Chem. 1965, 4, 50. (d) Miller, W. T.; Fried, J. H.; Godwhite, H. J. Am. Chem. Soc. 1960, 82, 3091.
3. See for example: (a) Hudlicky, M. Chemistry of Organic Fluorine Compounds, 2nd ed.; Ellis Horwood: Chichester, England, 1976; pp 285-290, 407-410. (b) Chambers, R. D. Fluorine in Organic Chemistry; Wiley: New York, 1973; pp 2-3, 148-170. (c) Chambers, R. D.; Mobbs, R. H. Adv. Fluorine Chem. 1965, 4, 50. (d) Miller, W. T.; Fried, J. H.; Godwhite, H. J. Am. Chem. Soc. 1960, 82, 3091.
4. See for example: (a) Hudlicky, M. Chemistry of Organic Fluorine Compounds, 2nd ed.; Ellis Horwood: Chichester, England, 1976; pp 285-290, 407-410. (b) Chambers, R. D. Fluorine in Organic Chemistry; Wiley: New York, 1973; pp 2-3, 148-170. (c) Chambers, R. D.; Mobbs, R. H. Adv. Fluorine Chem. 1965, 4, 50. (d) Miller, W. T.; Fried, J. H.; Godwhite, H. J. Am. Chem. Soc. 1960, 82, 3091.
5. Hung, M.-H.; Farnham, W. B.; Feiring, A. E.; Rozen, S. J. Am. Chem. Soc. 1993, 115, 8954-8959.
6. (a) Feiring, A. E.; Wonchoba, E. R. J. Org. Chem. 1992, 57, 7014-7017.
7. (b) Fuss, A.; Koch, V. Synthesis 1990, 604.
8. Smith, D. W., Jr.; Babb, D. A. Macromolecules 1996, 29, 852 and references therein.
9. Castelhaus, A. L.; Horne, S.; Taylor, G. J.; Billedeau, R.; Krantz, A. Tetrahedron 1988, 44, 5451 and references therein.
10. Babb, D. A.; Ezzell, B. R.; Clement, K. S.; Richey, W. F.; Kennedy, A. P. J. Polym. Sci. Part A: Polym. Chem. 1993, 31, 3465.
11. For general reviews, see: (a) Fluoropolymers; Wall, L. A. Ed.; Wiley: New York, 1972; Vol. XXV. (b) Feiring, A. E.; Imalzano, J. F.; Kerbow, D. L. Trends Polym. Sci. 1994, 2(1), 26. (c) Feiring, A. E. In Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E., Smart, B. E., Tatlow, J. C., Eds.; Plenum Press: New York, 1994; Chapter 15.
12. For general reviews, see: (a) Fluoropolymers; Wall, L. A. Ed.; Wiley: New York, 1972; Vol. XXV. (b) Feiring, A. E.; Imalzano, J. F.; Kerbow, D. L. Trends Polym. Sci. 1994, 2(1), 26. (c) Feiring, A. E. In Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E., Smart, B. E., Tatlow, J. C., Eds.; Plenum Press: New York, 1994; Chapter 15.
13. For general reviews, see: (a) Fluoropolymers; Wall, L. A. Ed.; Wiley: New York, 1972; Vol. XXV. (b) Feiring, A. E.; Imalzano, J. F.; Kerbow, D. L. Trends Polym. Sci. 1994, 2(1), 26. (c) Feiring, A. E. In Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E., Smart, B. E., Tatlow, J. C., Eds.; Plenum Press: New York, 1994; Chapter 15.
14. See for example: (a) Feiring, A. E. J. Macromol. Sci., Pure Appl. Chem. 1994, A31, 1657. (b) Labadie, J. W.; Hedrick, J. L. Macromolecules 1990, 23, 5371. (c) Mercer, F.; Goodman, T.; Wojtowicz, J.; Duff, D. J. Polym. Sci., Part A: Polym. Chem. 1993, 30, 1767.
15. See for example: (a) Feiring, A. E. J. Macromol. Sci., Pure Appl. Chem. 1994, A31, 1657. (b) Labadie, J. W.; Hedrick, J. L. Macromolecules 1990, 23, 5371. (c) Mercer, F.; Goodman, T.; Wojtowicz, J.; Duff, D. J. Polym. Sci., Part A: Polym. Chem. 1993, 30, 1767.
16. See for example: (a) Feiring, A. E. J. Macromol. Sci., Pure Appl. Chem. 1994, A31, 1657. (b) Labadie, J. W.; Hedrick, J. L. Macromolecules 1990, 23, 5371. (c) Mercer, F.; Goodman, T.; Wojtowicz, J.; Duff, D. J. Polym. Sci., Part A: Polym. Chem. 1993, 30, 1767.
17. See for example: (a) Wilson, D.; Stengenberger, H. D.; Hergenrother, P. M. Polyimides; Chapman and Hall: New York, 1990. (b) Cassidy, P. E.; Aminabhavi, M, T.; Farley, J. M. J. Macromol. Sci., Rev. Macromol. Chem. Phys. 1989, C29, 365. (c) Arnold, F. E., Jr.; Cheng, S. Z. D.; Hsu, S. L. C.; Lee, C. J.; Harris, F. W.; Lau, S. Polymer 1992, 33, 5179. (d) Feiring, A. E.; Auman, B. C.; Wonchoba, E. R. Macromolecules 1993, 26, 2779. (e) Cheng, S. Z. D.; Arnold, F. E., Jr.; Li, F.; Harris, F. W. Trends Polym. Sci. 1993, 1(8), 243.
18. See for example: (a) Wilson, D.; Stengenberger, H. D.; Hergenrother, P. M. Polyimides; Chapman and Hall: New York, 1990. (b) Cassidy, P. E.; Aminabhavi, M, T.; Farley, J. M. J. Macromol. Sci., Rev. Macromol. Chem. Phys. 1989, C29, 365. (c) Arnold, F. E., Jr.; Cheng, S. Z. D.; Hsu, S. L. C.; Lee, C. J.; Harris, F. W.; Lau, S. Polymer 1992, 33, 5179. (d) Feiring, A. E.; Auman, B. C.; Wonchoba, E. R. Macromolecules 1993, 26, 2779. (e) Cheng, S. Z. D.; Arnold, F. E., Jr.; Li, F.; Harris, F. W. Trends Polym. Sci. 1993, 1(8), 243.
19. See for example: (a) Wilson, D.; Stengenberger, H. D.; Hergenrother, P. M. Polyimides; Chapman and Hall: New York, 1990. (b) Cassidy, P. E.; Aminabhavi, M, T.; Farley, J. M. J. Macromol. Sci., Rev. Macromol. Chem. Phys. 1989, C29, 365. (c) Arnold, F. E., Jr.; Cheng, S. Z. D.; Hsu, S. L. C.; Lee, C. J.; Harris, F. W.; Lau, S. Polymer 1992, 33, 5179. (d) Feiring, A. E.; Auman, B. C.; Wonchoba, E. R. Macromolecules 1993, 26, 2779. (e) Cheng, S. Z. D.; Arnold, F. E., Jr.; Li, F.; Harris, F. W. Trends Polym. Sci. 1993, 1(8), 243.
20. See for example: (a) Wilson, D.; Stengenberger, H. D.; Hergenrother, P. M. Polyimides; Chapman and Hall: New York, 1990. (b) Cassidy, P. E.; Aminabhavi, M, T.; Farley, J. M. J. Macromol. Sci., Rev. Macromol. Chem. Phys. 1989, C29, 365. (c) Arnold, F. E., Jr.; Cheng, S. Z. D.; Hsu, S. L. C.; Lee, C. J.; Harris, F. W.; Lau, S. Polymer 1992, 33, 5179. (d) Feiring, A. E.; Auman, B. C.; Wonchoba, E. R. Macromolecules 1993, 26, 2779. (e) Cheng, S. Z. D.; Arnold, F. E., Jr.; Li, F.; Harris, F. W. Trends Polym. Sci. 1993, 1(8), 243.
21. See for example: (a) Wilson, D.; Stengenberger, H. D.; Hergenrother, P. M. Polyimides; Chapman and Hall: New York, 1990. (b) Cassidy, P. E.; Aminabhavi, M, T.; Farley, J. M. J. Macromol. Sci., Rev. Macromol. Chem. Phys. 1989, C29, 365. (c) Arnold, F. E., Jr.; Cheng, S. Z. D.; Hsu, S. L. C.; Lee, C. J.; Harris, F. W.; Lau, S. Polymer 1992, 33, 5179. (d) Feiring, A. E.; Auman, B. C.; Wonchoba, E. R. Macromolecules 1993, 26, 2779. (e) Cheng, S. Z. D.; Arnold, F. E., Jr.; Li, F.; Harris, F. W. Trends Polym. Sci. 1993, 1(8), 243.
22. Some new TFVE chemistry has been recently presented: Neilson, R. H.; Ji, J.; Narayan-Sarathy, S.; Oxley, J. D.; Smith, D. W., Jr. Abstracts of Papers, 213th National Meeting of the American Chemical Society, San Francisco, CA; American Chemical Society: Washington, DC, 1997; INORG 341.
23. 2 and charged with aryl bromide 1 (7.6 g, 30 mmol) and dry ether (45 mL). The mixture was cooled to -78 °C ,and t-BuLi (17.7 mL, 31 mmol, 1.7 M in pentane) was added dropwise from the addition funnel. The mixture was then stirred for ca. 1 h at -78 °C prior to the addition of the next reactant.
24. 3Si: C, 55.80 (55.12); H, 5.07 (5.35).
25. 6SiCl: C, 48.07 (48.06); H, 2.61 (2.74).
26. 2PBr: C, 37.84 (37.84); H, 4.99 (5.07).
27. 6: C, 58.08 (57.98); H, 2.71 (2.82).
28. Roothan, C. C. J. Rev. Mod. Phys. 1951, 23, 69.
29. Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213.
30. (a) Møller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618.
31. (b) Binkley, J. S.; Pople, J. A. Int. J. Quantum Chem. 1975, 9, 229.
32. Spartan is a graphical quantum-mechanical program marketed by Wavefunction, Inc., 18401 Von Karman, No. 370, Irvine, CA 92715.
33. 2 compound: Neilson, R. H.; Wisian-Neilson, P. Inorg. Chem. 1982, 21, 3568.