Syntheses of mono-, di-, and trifluorinated styrenic monomers

Synthesis

Volumn , Issue 11, 2010, Pages 1883-1890

  Walkowiak, Justyna ^a   Del Campo, Teresa Martinez ^a   Ameduri, Bruno ^b   Gouverneur, Véronique ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b UNIVERSITÉ DE MONTPELLIER   (France)

Author keywords

Fluorination; Functional fluoropolymers; Monomer synthesis; Nucleophilic fluoroalkylation; Palladium catalysis

Indexed keywords

CONCISE SYNTHESIS; FLUORO-POLYMERS; GRAM QUANTITIES; MONOMER SYNTHESIS; NUCLEOPHILIC FLUOROALKYLATION; PALLADIUM CATALYSIS; POLYMERISATION; REASONABLY PRICED; STARTING MATERIALS; STYRENIC MONOMERS;

CATALYSIS; FLUORINATION; FLUORINE; HALOGENATION; PALLADIUM; PHOTORESISTS; SYNTHESIS (CHEMICAL);

MONOMERS;

(3 FLUOROPROP 1 EN 2 YL)BENZENE; (3,3 DIFLUOROPROP 1 EN 2 YL)BENZENE; (3,3,3 TRIFLUOROPROP 1 EN 2 YL)BENZENE; 1 BROMO 4 (3 FLUOROPROP 1 EN 2 YL)BENZENE; 1 BROMO 4 (3,3,3 TRIFLUOROPROP 1 EN 2 YL)BENZENE; 1,1 DIFLUORO 2 PHENYL 1 (PHENYLSULFONYL)PROPAN 2 OL; 2 (4 BROMOPHENYL)ACRYLALDEHYDE; 2 (4 BROMOPHENYL)PROP 2 EN 1 OL; 2 PHENYLACRYLALDEHYDE; 2 PHENYLPROP 2 EN 1 OL; 3,3 DIFLUORO 2 PHENYL 3 (PHENYLSULFONYL)PROP 1 ENE; [2 (4 BROMOPHENYL)ALLYL]TRIMETHYLSILANE; ALPHA (MONOFLUOROMETHYL)STYRENE DERIVATIVE; ALPHA (TRIFLUOROMETHYL)STYRENE DERIVATIVE; DIETHYL 4 (3 FLUOROPROP 1 EN 2 YL)PHENYLPHOSPHONATE; SILANE DERIVATIVE; STYRENE DERIVATIVE; TRIMETHYL(2 PHENYLALLYL)SILANE; TRIMETHYL(2 PHENYLALLYL)SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL COMPOSITION; CHEMICAL STRUCTURE; ELECTROPHILICITY; FLUORINATION; POLYMERIZATION; SYNTHESIS;

EID: 77952746661     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1218785     Document Type: Article

References (47)

1. Wall L A., Fluoropolymers Wiley New York 1972
2. Feiring A E., In Organofluorine Chemistry: Principles and Commercial Applications Banks R E. Smart B E. Tatlow J C. Plenum Press New York 1994 Chap. 15 339-372
3. Scheirs J, Modern Fluoropolymers Wiley New York 1997
4. Hougham G, Davidson T, Cassidy P, Johns K, Fluoropolymers Kluvert New York 1999
5. Ameduri B, Boutevin B, Well Architectured Fluoropolymers: Synthesis, Properties and Applications Elsevier Amsterdam 2004
6. Kobayashi S, Munekuta S, Unoki M, Iwamoto T, Patent EP 0239935 1987, Yamamoto T, Matsumoto T, Shimada K, Uozu Y, Murata R, Patent EP 0256765 1988, Skutnik B J., Patent AU 569145 1988, Yamamoto S, Matsumoto M, Patent JP 63430104 1988
7. Boutevin B, Pietrasanta Y, Les Acrylates et poly Acrylates fluorés Erec Paris 1998
8. Banks B A., The Use of Fluoropolymers in Space Applications, Modern Fluoropolymers Wiley New York 1999 Chap. 4 103-114
9. Souzy R, Ameduri B, Boutevin B, J. Polym. Sci., Part A: Polym. Chem. 2004 42 5077
10. Kostov G, Tredwell M, Ameduri B, Gouverneur V, J. Poly. Sci., Part A: Polym. Chem. 2007 45 3843
11. Olofsson K, Larhed M, Hallberg A, J. Org. Chem. 1998 63 5076
12. Tredwell M, Gouverneur V, Org. Biomol. Chem. 2006 4 26
13. Nyffeler P T., Duron S G., Burkart M D., Vincent S P., Wong C.-H, Angew. Chem. Int. Ed. 2005 44 192
14. Mo J, Xu L, Xiao J, J. Am. Chem. Soc. 2005 127 751
15. Luo H.-Q, Loh T.-P, Tetrahedron Lett. 2009 50 1554
16. Mo J, Xu L, Ruan J, Liu S, Xiao J, Chem. Commun. 2006 3591, Pei W, Sun L, Xiao J, Patent CN 1,634,825 2005
17. Organ M G., Murray A P., J. Org. Chem. 1997 62 1523
18. Bresciani S, Slawin A M. Z., OHagan D, J. Fluorine Chem. 2009 130 537
19. Kotov S V., Pedersen S D., Qiu W, Qiu Z.-M, Burton D J., J. Fluorine Chem. 1997 82 13
20. Stone C, Daynard T S., Hu L.-Q, Mah C, Steck A E., J. New Mater. Electrochem. Syst. 2000 3 43
21. Lafitte B, Jannasch P, On the Prospects for Phosphonated Polymers as Proton-Exchange Fuel Cell Membranes, In Advances in Fuel Cells Zhao T Kreuer K.-D Van Nguyen T Elsevier Amsterdam 2007 Chap. 3
22. Ohmori H, Nakai S, Masui M, J. Chem. Soc., Perkin Trans. 1 1979 2023
23. Obrycki R, Griffin C E., J. Org. Chem. 1968 33 632
24. Plumb J B., Obrycki R, Griffin C E., J. Org. Chem. 1966 31 2455
25. Balthazor T M., Grabiak R C., J. Org. Chem. 1980 45 5425
26. Tavs P, Chem. Ber./Recl 1970 103 2428
27. Schwan A L., Chem. Soc. Rev. 2004 33 218
28. Hirao T, Masunaga T, Yamada N, Ohshiro Y, Agawa T, Bull. Chem. Soc. Jpn. 1982 55 909
29. Burger A, Dawson N D., J. Org. Chem. 1951 16 1250
30. Dawson N D., Burger A, J. Org. Chem. 1953 18 207
31. Eymery F, Iorga B, Savignac P, Tetrahedron 1999 55 13109
32. Organofluorine Compounds. Chemistry and Applications Hiyama T Springer New York 2000
33. Organofluorine Chemistry - Principles and Commercial Applications Banks R E. Smart B E. Tatlow J C. Plenum Press New York 1994
34. Fluorine in Bioorganic Chemistry Welch J T. Eshwarakrishman S Wiley New York 1991
35. Fluorine-Containing Molecules. Structure, Reactivity, Synthesis, and Applications Liebman J F. Greenberg A Dolbier W R. Jr. VCH New York 1988
36. Shimazu M, Maeda T, Fujisawa T, J. Fluorine Chem. 1995 71 9
37. Kuroboshi M, Hiyama T, J. Fluorine Chem. 1994 69 127
38. Hugenberg V, Haufe G, Synlett 2008 106, Hiyama T, Kuroboshi M, Patent JP 4264041 1992
39. Burton D J., Wiemers D M., J. Fluorine Chem. 1981 18 573
40. Li X.-Y, Jiang X.-K, Gong Y.-F, Pan H.-Q, Acta Chim. Sin. (Engl. Ed.) 1985 43 260
41. Prakash G K. S., Hu J, Olah G A., J. Org. Chem. 2003 68 4457
42. Prakash G K. S., Hu J, Wang Y, Olah G A., Eur. J. Org. Chem. 2005 2218
43. Ni C, Hu J, Tetrahedron Lett. 2005 46 8273
44. When reductive desulfonation was performed prior to the dehydration, compound 17 was observed, but it was contaminated by significant amount of inseparable byproduct., Kazennikova G V., Talalaeva T V., Zimin A V., Kocheshkov K A., Izv. Akad. Nauk SSSR, Otd. Khim. Nauk 1961 6 1060
45. Gøgsig T M., Søbjerg L S., Lindhardt A T., Jensen K L., Skrydstrup T, J. Org. Chem. 2008 73 3404
46. Jiang B, Xu Y, Tetrahedron Lett. 1992 33 511
47. Pan R.-q, Liua X.-x, Deng M.-z, J. Fluorine Chem. 1999 95 167