Synthesis of internal fluorinated alkenes via facile aryloxylation of substituted phenols with aryl trifluorovinyl ethers

Organic and Biomolecular Chemistry

Volumn 9, Issue 13, 2011, Pages 4842-4849

  Moody, Justin D ^a   Vanderveer, Don ^a   Smith Jr , Dennis W ^a,b   Iacono, Scott T ^a,c  

^a Clemson University   (United States)

^b UNIVERSITY OF TEXAS AT DALLAS   (United States)

^c UNITED STATES AIR FORCE ACADEMY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION PRODUCTS; ADDITION-ELIMINATION; ISOLATED YIELD; N ,N-DIMETHYLFORMAMIDE; NETWORK MATERIALS; PARA-SUBSTITUTED PHENOLS; SODIUM HYDRIDES; SUBSTITUTED PHENOL; SUBSTITUTED PRODUCTS; SUBSTITUTION PRODUCTS; THERMAL ACTIVATION;

ADDITION REACTIONS; ARGON; BROMINE; CESIUM; DIFFERENTIAL SCANNING CALORIMETRY; DIMETHYLFORMAMIDE; ETHERS; HYDRIDES; ISOMERS; OLEFINS; ORGANIC COMPOUNDS; SODIUM; SODIUM COMPOUNDS;

PHENOLS;

EID: 79959791220     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c1ob05041a     Document Type: Article

References (52)

1. R. D. Chambers, in Synthetic Fluorine Chemistry, ed., G. A. Olah,,, R. D. Chambers, and, G. K. S. Prakash,, Wiley, New York, 1992, pp. 359-380
2. G. G. Furin Russ. J. Org. Chem. 2002 38 921 961
3. L. Hintermann, in C-X Bond Formation, Springer-Verlag Berlin, Berlin, vol. 31, pp. 123-155
4. Y. Matsukawa J. Mizukado H.-D. Quan M. Tamura A. Sekiya Angew. Chem. 2005 33 1128 1130
5. J. H. Kim S. Kwak J. S. Lee H. T. Vo C. S. Kim H.-J. Kang H. S. Kim H. Lee Appl. Catal., B 2009 89 137 141
6. M.-H. Hung W. B. Farnham A. E. Feiring S. Rozen J. Am. Chem. Soc. 1993 115 8954 8959
7. Z. Y. Yang A. E. Feiring B. E. Smart J. Am. Chem. Soc. 1994 116 4135 4136
8. A. E. Feiring E. R. Wonchoba J. Am. Chem. Soc. 1992 57 7014 7017
9. A. E. Feiring S. Rozen E. R. Wonchoba J. Fluorine Chem. 1998 89 31 34
10. V. Crkva R. Polk O. Paleta J. Fluorine Chem. 1996 80 135 144
11. R. Rodenhouse V. Percec A. E. Feiring J. Polym. Sci., Part C: Polym. Lett. 1990 28 345 355
12. S. T. Iacono S. M. Budy D. Ewald D. W. Smith, Jr. Chem. Commun. 2006 4844 4846
13. B. Muir D. B. Cooper W. A. Carrick C. M. Timperley B. J. Slater S. Quick J. Chromatogr., A 2005 1098 156 165
14. S. Couve-Bonnaire D. Cahard X. Pannecoucke Org. Biomol. Chem. 2007 5 1151 1157
15. J. W. Goodby P. Hindmarch M. Hird R. A. Lewis K. J. Toyne Mol. Cryst. Liq. Cryst. 2001 364 889
16. M. Hird Chem. Soc. Rev. 2007 36 2070 2095
17. T. Nguyen C. Wakselman J. Fluorine Chem. 1995 74 273 277
18. W. T. Miller, Jr. J. H. Fried H. Goldwhite J. Am. Chem. Soc. 1960 82 3091 3098
19. W. T. Miller Jr. R. J. Burnard J. Am. Chem. Soc. 1968 90 7367 7368
20. R. E. Banks M. J. McGlinchey J. Chem. Soc. (C) 1970 2172 2175
21. I. Dlouh J. Kviĉala O. Paleta J. Fluorine Chem. 2002 117 149 159
22. L. S. Chen C. Tamborski J. Fluorine Chem. 1982 20 341 348
23. P. Tarrant H. C. Brown J. Am. Chem. Soc. 1951 73 5831 5833
24. D. C. England L. R. Melby M. A. Dietrich R. V. Lindsey, Jr. J. Am. Chem. Soc. 1960 82
25. A. E. Feiring S. Rozen E. R. Wonchoba J. Fluorine Chem. 1998 89 31 34
26. G. G. Furin L. S. Pressman L. M. Pokrovsky A. P. Krysin K.-W. Chi J. Fluorine Chem. 2000 106 13 24
27. C. M. Timperley M. J. Waters J. A. Greenall J. Fluorine Chem. 2006 127 249 256
28. O. Paleta V. Crkva J. Kvĉala J. Fluorine Chem. 1996 80 125 134
29. V. Crkva O. Paleta J. Fluorine Chem. 1999 94 141 156
30. B. K. Spraul S. Suresh J. Jin D. W. Smith, Jr. J. Am. Chem. Soc. 2006 128 7055 7064
31. D. A. Babb, in Fluoropolymers 1: Synthesis, ed., G. Hougham,,, P. E. Cassidy,,, K. Johns, and, T. Davidson,, Plenum Press, New York, 1999, pp. 25-50
32. D. A. Babb B. R. Ezzell K. S. Clement W. F. Richey A. P. Kennedy J. Polym. Sci., Part A: Polym. Chem. 1993 31 3465 3477
33. D. W. Smith, Jr. S. Chen S. M. Kumar J. Ballato C. Topping H. V. Shah S. H. Foulger Adv. Mater. 2002 14 1585 1589
34. S. T. Iacono S. M. Budy J. Jin D. W. Smith, Jr. J. Polym. Sci., Part A: Polym. Chem. 2007 45 5705 5721
35. S. T. Iacono D. Ewald A. Sankhe A. Rettenbacher D. W. Smith, Jr. High Perform. Polym. 2008 19 581 591
36. S. T. Iacono S. M. Budy J. D. Moody R. C. Smith D. W. Smith, Jr. Macromolecules 2008 41 7490 7496
37. D. OHagan Chem. Soc. Rev. 2008 37 308 319
38. H.-O. Harada N. Ishikawa J. Fluorine Chem. 1978 11 87 92
39. Y. Apeloig Z. Rappoport J. Am. Chem. Soc. 1979 101 5095 5098
40. W. Dmowski J. Fluorine Chem. 1984 26 22 241
41. D. J. Burton H. C. Krutzsch J. Org. Chem. 1971 36 2351 2354
42. R. Sauvetre J. Normant J. Villieras Tetrahedron 1975 31 897 903
43. X.-K. Jiang G.-Z. Ji Y.-Q. Shi J. Fluorine Chem. 1987 37 405 417
44. W. J. Pummer L. A. Wall SPE Transactions 1963 3 220 224
45. K. J. Klabunde D. J. Burton J. Am. Chem. Soc. 1972 94 5985 5990
46. R. C. Bingham J. Am. Chem. Soc. 1976 98 535 540
47. G. A. Olah V. Prakash Reddy G. K. S. Surya Chem. Rev. 1992 92 69 95
48. C. G. Krespan F. A. Van-Catledge B. E. Smart J. Am. Chem. Soc. 1984 106 5544
49. N. Aragrag, D. C. Castiglione, P. Davies, F. J. Davis and S. I. Patel, in The Practical Approach in Chemistry Series, ed., F. J. Davis,, Oxford University Press, Oxford, 2004, pp. 43-98
50. T. Yamamoto A. Morita Y. Miyazaki T. Maruyama H. Wakayama Z. H. Zhou Y. Nakamura T. Kanbara S. Sasaki K. Kubota Macromolecules 1992 25 1214 1223
51. W. L. F. Armarego and D. D. Perrin, Purification of Laboratory Chemicals, Butterworth Heinemann, Boston, 4th edn, 1996
52. G. M. Sheldrick Acta Cryst. 2008 A64 112 122