p-Phenylene sulfide oligomers and their properties. Ar-S couplings mediated by copper or by fluorine substitutions

Tetrahedron Letters

Volumn 50, Issue 17, 2009, Pages 1977-1981

  Goyot, Olivier ^b   Gingras, Marc ^a,b  

^a AIX MARSEILLE UNIVERSITÉ   (France)

^b UNIVERSITÉ CÔTE D'AZUR   (France)

Author keywords

Ar S coupling; Copper catalysis; Fluorine; Nucleophilic aromatic substitution; Poly(p phenylene sulfide)

Indexed keywords

4 PHENYLENE SULFIDE OLIGOMER; ARGON; ARYL THIOLATE DERIVATIVE; COPPER; FLUORINE; OLIGOMER; PHENAZONE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SULFIRAM; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; CAMERA; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL STRUCTURE; CONTROLLED STUDY; CRYSTAL STRUCTURE; CRYSTALLIZATION; MELTING POINT; MICROSCOPY; QUALITATIVE ANALYSIS; SOLUBILITY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 61749090297     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.02.068     Document Type: Article

References (35)

1. Geibel J.F., and Campbell R.W. In: Eastmond G.C., Ledwith A., Russo S., and Sigwalt P. (Eds). Comprehensive Polymer Science Vol. 5, Chapter 32 (1989), Pergamon, Oxford, UK
2. Shacklette L.W., Eisenbaumer R.L., Chance R.R., Eckhardt H., Frommer J.E., and Baughman R.H. J. Chem. Phys. 75 (1981) 1919-1927
3. In: Nalwa H.S. (Ed). Handbook of Organic Conductive Molecules and Polymers Vols. 1-4 (1997), John Wiley & Sons, New York 3334
4. Edmonds, J. T., Jr. ; Hills, H. W., Jr. U.S. Patent, 3 354 129, 1967.
5. Edmonds Jr. J.T., and Hills Jr. H.W. Chem. Abstr. 68 (1968) 13598e
6. Fahey D.R., and Ash C.E. Macromolecules 24 (1991) 4242-4249
7. Fradet A. Bull. Soc. Chim. Belg. 98 (1989) 635-641
8. Genvresse P. Bull. Soc. Chim. Fr. 17 (1897) 599-609
9. Lenz R.W., Handlovis C.E., and Smith H.A. J. Polym. Sci. 58 (1962) 351-367
10. MacCallum A.D. J. Org. Chem. 13 (1948) 154-159
11. Koch W., and Heitz W. Makromol. Chem. 184 (1983) 779-792
12. Koch W., Risse W., and Heitz W. Makromol. Chem. Suppl. 12 (1985) 105-123
13. Tsuchida E., Yamamoto K., Oyaizu K., Suzuki F., Hay A.S., and Wang Z.Y. Macromolecules 28 (1995) 409-416
14. Pinchart A., Dallaire C., Van Bierbeek A., and Gingras M. Tetrahedron Lett. 40 (1999) 5479-5482
15. Pinchart A., Dallaire C., and Gingras M. Tetrahedron Lett. 39 (1998) 543-546
16. Vicente J., Abad J.A., and López-Nicolas R.M. Tetrahedron 64 (2008) 6281-6288
17. Vicente J., Abad J.A., and López-Nicolas R.M. Tetrahedron Lett. 46 (2005) 5839-5840
18. In: Müllen K., and Wegner G. (Eds). Electronic Materials: The Oligomer Approach (1998), John Wiley, New & Sons, New York 628
19. Among some reviews:. Barañano D., Mann G., and Hartwig J.F. Curr. Org. Chem. 1 (1997) 287-305
20. Kondo T., and Mitsudo T.-a. Chem. Rev. 100 (2000) 3205-3220 Original references: Cu-cat.
21. Adam R., Reifschneider W., and Nair D. Croatia Chim. Acta (1957) 29
22. Adams R., and Ferretti A. J. Am. Chem. Soc. 81 (1959) 4927-4931
23. Lindley J. Tetrahedron 9 (1984) 1433-1456 Pd cat.
24. Kosugi M., Shimizu T., and Migita T. Chem. Lett. (1978) 13-14
25. Migita T., Shimizu T., Asami Y., Shiobara J.-I., Kato Y., and Kosugi M. Bull. Chem. Soc. Jpn. 53 (1980) 1385-1389
26. Fernandez-Rodriguez M.A., Shen Q., and Hartwig J.F. J. Am. Chem. Soc. 128 (2006) 2180-2181 Ni-cat.
27. Cristau H.J., Chabaud B., and Christol H. Synthesis 11 (1981) 892-894
28. Takagi K. Chem. Lett. (1987) 2221-2224 Co-cat.
29. Wong Y.-C., Jayanth T.T., and Cheng C.-H. Org. Lett. 8 (2006) 5613-5616
30. Among some methods:. de Jong F., and Janssen M.J. J. Org. Chem. 36 (1971) 1645-1648
31. Chahma M., Hicks R.G., and Myles D.J.T. Macromolecules 37 (2004) 2010-2012
32. Campbell J.R. J. Org. Chem. 29 (1964) 1830-1833
33. Uhlenbroeck J.H. Recl. Trav. Chim. Pays-Bas. 80 (1961) 1057-1065
34. +, 5.2%). Note: 17 can be produced on a 3g scale (60% yield) by a similar procedure.
35. +, 27.9%).