Functionalized p-phenylene sulfides synthesis of new molecular wires

Tetrahedron Letters

Volumn 39, Issue 7, 1998, Pages 543-546

  Pinchart, Alain ^a   Dallaire, Carol ^a   Gingras, Marc ^a  

^a UNIVERSITÉ LIBRE DE BRUXELLES   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; COPPER; PALLADIUM; POLYCYCLIC AROMATIC COMPOUND; THIOL DERIVATIVE;

ARTICLE; CHEMICAL BOND; SYNTHESIS;

EID: 0032510084     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10624-4     Document Type: Article

References (45)

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2. 1. Reviews: Lopez, L. C.; Wilkes, G. L. Rev. Makromol. Chem. Phys. 1989, C29, 83. Other reports: Lenz. R. W.; Handlovits, C. E.; Smith. H. A. J. Polym. Sci. 1962, 58, 351. Edmonds Jr. J. T.; Hill, H. W. (Philips Petroleum Co.) USA 3354129, 1967. ibid. Chem. Abstr. 1968, 68, 13598e. Novt. M.; Petrillo, G.; Sartirana, M. L. Tetrahedron Len. 1986, 6129. Fradet, A. Bull. Soc. Chim. Belg. 1989, 98, 635. Fahey, D. R.; Ash, C. E. Macromolecules 1991, 24, 4242. Hay, A. S.; Ding, Y. Macromolecules 1997, 30, 1849.
3. 1. Reviews: Lopez, L. C.; Wilkes, G. L. Rev. Makromol. Chem. Phys. 1989, C29, 83. Other reports: Lenz. R. W.; Handlovits, C. E.; Smith. H. A. J. Polym. Sci. 1962, 58, 351. Edmonds Jr. J. T.; Hill, H. W. (Philips Petroleum Co.) USA 3354129, 1967. ibid. Chem. Abstr. 1968, 68, 13598e. Novt. M.; Petrillo, G.; Sartirana, M. L. Tetrahedron Len. 1986, 6129. Fradet, A. Bull. Soc. Chim. Belg. 1989, 98, 635. Fahey, D. R.; Ash, C. E. Macromolecules 1991, 24, 4242. Hay, A. S.; Ding, Y. Macromolecules 1997, 30, 1849.
4. 1. Reviews: Lopez, L. C.; Wilkes, G. L. Rev. Makromol. Chem. Phys. 1989, C29, 83. Other reports: Lenz. R. W.; Handlovits, C. E.; Smith. H. A. J. Polym. Sci. 1962, 58, 351. Edmonds Jr. J. T.; Hill, H. W. (Philips Petroleum Co.) USA 3354129, 1967. ibid. Chem. Abstr. 1968, 68, 13598e. Novt. M.; Petrillo, G.; Sartirana, M. L. Tetrahedron Len. 1986, 6129. Fradet, A. Bull. Soc. Chim. Belg. 1989, 98, 635. Fahey, D. R.; Ash, C. E. Macromolecules 1991, 24, 4242. Hay, A. S.; Ding, Y. Macromolecules 1997, 30, 1849.
5. 1. Reviews: Lopez, L. C.; Wilkes, G. L. Rev. Makromol. Chem. Phys. 1989, C29, 83. Other reports: Lenz. R. W.; Handlovits, C. E.; Smith. H. A. J. Polym. Sci. 1962, 58, 351. Edmonds Jr. J. T.; Hill, H. W. (Philips Petroleum Co.) USA 3354129, 1967. ibid. Chem. Abstr. 1968, 68, 13598e. Novt. M.; Petrillo, G.; Sartirana, M. L. Tetrahedron Len. 1986, 6129. Fradet, A. Bull. Soc. Chim. Belg. 1989, 98, 635. Fahey, D. R.; Ash, C. E. Macromolecules 1991, 24, 4242. Hay, A. S.; Ding, Y. Macromolecules 1997, 30, 1849.
6. 1. Reviews: Lopez, L. C.; Wilkes, G. L. Rev. Makromol. Chem. Phys. 1989, C29, 83. Other reports: Lenz. R. W.; Handlovits, C. E.; Smith. H. A. J. Polym. Sci. 1962, 58, 351. Edmonds Jr. J. T.; Hill, H. W. (Philips Petroleum Co.) USA 3354129, 1967. ibid. Chem. Abstr. 1968, 68, 13598e. Novt. M.; Petrillo, G.; Sartirana, M. L. Tetrahedron Len. 1986, 6129. Fradet, A. Bull. Soc. Chim. Belg. 1989, 98, 635. Fahey, D. R.; Ash, C. E. Macromolecules 1991, 24, 4242. Hay, A. S.; Ding, Y. Macromolecules 1997, 30, 1849.
7. 1. Reviews: Lopez, L. C.; Wilkes, G. L. Rev. Makromol. Chem. Phys. 1989, C29, 83. Other reports: Lenz. R. W.; Handlovits, C. E.; Smith. H. A. J. Polym. Sci. 1962, 58, 351. Edmonds Jr. J. T.; Hill, H. W. (Philips Petroleum Co.) USA 3354129, 1967. ibid. Chem. Abstr. 1968, 68, 13598e. Novt. M.; Petrillo, G.; Sartirana, M. L. Tetrahedron Len. 1986, 6129. Fradet, A. Bull. Soc. Chim. Belg. 1989, 98, 635. Fahey, D. R.; Ash, C. E. Macromolecules 1991, 24, 4242. Hay, A. S.; Ding, Y. Macromolecules 1997, 30, 1849.
8. 1. Reviews: Lopez, L. C.; Wilkes, G. L. Rev. Makromol. Chem. Phys. 1989, C29, 83. Other reports: Lenz. R. W.; Handlovits, C. E.; Smith. H. A. J. Polym. Sci. 1962, 58, 351. Edmonds Jr. J. T.; Hill, H. W. (Philips Petroleum Co.) USA 3354129, 1967. ibid. Chem. Abstr. 1968, 68, 13598e. Novt. M.; Petrillo, G.; Sartirana, M. L. Tetrahedron Len. 1986, 6129. Fradet, A. Bull. Soc. Chim. Belg. 1989, 98, 635. Fahey, D. R.; Ash, C. E. Macromolecules 1991, 24, 4242. Hay, A. S.; Ding, Y. Macromolecules 1997, 30, 1849.
9. 2. Franke, J.; Vögtle, F. Tetrahedron Lett. 1984, 3445. Hay, A. S.; Wang, Z. Y.; Tsuchida, E.; Yamamoto, K.; Oyaizu, K.; Suzuki, F. Macromolecules 1995, 28, 409.
10. 2. Franke, J.; Vögtle, F. Tetrahedron Lett. 1984, 3445. Hay, A. S.; Wang, Z. Y.; Tsuchida, E.; Yamamoto, K.; Oyaizu, K.; Suzuki, F. Macromolecules 1995, 28, 409.
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12. 3. Shacklette. L. W.; Elsenbaumer, R. L.; Chance, R. R.; Eckhardt, H.; Frommer, J. E.; Baughman, R.H. J. Chem. Phys. 1980, 75, 1919. Kaplan M. L.; Reents Jr., W. D. Tetrahedron Lett. 1982, 373. Koch. W.; Heitz, W. Makromol. Chem. 1983, 184, 779.
13. 3. Shacklette. L. W.; Elsenbaumer, R. L.; Chance, R. R.; Eckhardt, H.; Frommer, J. E.; Baughman, R.H. J. Chem. Phys. 1980, 75, 1919. Kaplan M. L.; Reents Jr., W. D. Tetrahedron Lett. 1982, 373. Koch. W.; Heitz, W. Makromol. Chem. 1983, 184, 779.
14. 4. a) NMP: Shaw, J. E. J. Org. Chem. 1991, 56, 3728. Caruso, A. J.; Colley, A. M.; Bryant, G. L. J. Org. Chem. 1991, 56, 862.
15. 4. a) NMP: Shaw, J. E. J. Org. Chem. 1991, 56, 3728. Caruso, A. J.; Colley, A. M.; Bryant, G. L. J. Org. Chem. 1991, 56, 862.
16. b) DMF: Nabeshima, T.; Iwata, S; Furukawa, Morihashi, N.; K.; Kikuchi, O. Chem. Lett. 1988, 1325. Testaferri, L.; Tiecco, M.; Tingoli, M.; Chianelli, D.; Montanucci, M. Synthesis, 1983, 751. Peach, M. E.; Rayner, E. S. J. Fluorine Chem. 1979, 13, 447.
17. b) DMF: Nabeshima, T.; Iwata, S; Furukawa, Morihashi, N.; K.; Kikuchi, O. Chem. Lett. 1988, 1325. Testaferri, L.; Tiecco, M.; Tingoli, M.; Chianelli, D.; Montanucci, M. Synthesis, 1983, 751. Peach, M. E.; Rayner, E. S. J. Fluorine Chem. 1979, 13, 447.
18. b) DMF: Nabeshima, T.; Iwata, S; Furukawa, Morihashi, N.; K.; Kikuchi, O. Chem. Lett. 1988, 1325. Testaferri, L.; Tiecco, M.; Tingoli, M.; Chianelli, D.; Montanucci, M. Synthesis, 1983, 751. Peach, M. E.; Rayner, E. S. J. Fluorine Chem. 1979, 13, 447.
19. c) Amides: Campbell, J. R. J. Org. Chem. 1964, 29, 1830.
20. d) Polyglymes: Pastor, S. D. Helv. Chim. Acta 1988, 71, 859. Pastor, S. D.; Hessell, E. T. J. Org. Chem. 1985, 50, 4812.
21. d) Polyglymes: Pastor, S. D. Helv. Chim. Acta 1988, 71, 859. Pastor, S. D.; Hessell, E. T. J. Org. Chem. 1985, 50, 4812.
22. 1-dimethyl imidazolidinone (DMI): Dirk, C. W.; Cox. S. D.; Wellman, D. E.; Wudl, F. J. Org. Chem. 1985, 50, 2395.
23. f) HMPA: Cogolli, P.; Maiolo, F.; Testaferri, L.; Tingoli, M.; Tiecco, M. J. Org. Chem. 1979, 44, 2642. DMSO: Bradshaw, J. S.; South, J. A.; Hales, R. H. J. Org. Chem. 1972, 37, 2381.
24. f) HMPA: Cogolli, P.; Maiolo, F.; Testaferri, L.; Tingoli, M.; Tiecco, M. J. Org. Chem. 1979, 44, 2642. DMSO: Bradshaw, J. S.; South, J. A.; Hales, R. H. J. Org. Chem. 1972, 37, 2381.
25. 2O and thiols: Adams, R.; Reifschneider, W.; Nair, D. Croatia Chim. Acta 1957, 29. Adams, R.; Ferretti, A. J. Am. Chem. Soc. 1959, 81, 4927 and references therein. Adams, R.; Reifschneider, W.; Ferreti, A. Org. Synth. 1962, 42, 22. Posner, G. H.; Brunelle, D. J.; Sinoway, L. Synthesis 1974, 662.
26. 2O and thiols: Adams, R.; Reifschneider, W.; Nair, D. Croatia Chim. Acta 1957, 29. Adams, R.; Ferretti, A. J. Am. Chem. Soc. 1959, 81, 4927 and references therein. Adams, R.; Reifschneider, W.; Ferreti, A. Org. Synth. 1962, 42, 22. Posner, G. H.; Brunelle, D. J.; Sinoway, L. Synthesis 1974, 662.
27. 2O and thiols: Adams, R.; Reifschneider, W.; Nair, D. Croatia Chim. Acta 1957, 29. Adams, R.; Ferretti, A. J. Am. Chem. Soc. 1959, 81, 4927 and references therein. Adams, R.; Reifschneider, W.; Ferreti, A. Org. Synth. 1962, 42, 22. Posner, G. H.; Brunelle, D. J.; Sinoway, L. Synthesis 1974, 662.
28. 2O and thiols: Adams, R.; Reifschneider, W.; Nair, D. Croatia Chim. Acta 1957, 29. Adams, R.; Ferretti, A. J. Am. Chem. Soc. 1959, 81, 4927 and references therein. Adams, R.; Reifschneider, W.; Ferreti, A. Org. Synth. 1962, 42, 22. Posner, G. H.; Brunelle, D. J.; Sinoway, L. Synthesis 1974, 662.
29. b) Cu1 and thiols: Suzuki, H.; Abe, H.; Osuka, A. Chem. Lett. 1980, 1363.
30. c) Cu0 and disulfides or thiols: Yamamoto, T.; Sekine, Y. Can. J. Chem. 1984, 62, 1544. Berges, P.; Klar, G. Z. Naturforsch B., Chem. Sci. 1988, 43, 599.
31. c) Cu0 and disulfides or thiols: Yamamoto, T.; Sekine, Y. Can. J. Chem. 1984, 62, 1544. Berges, P.; Klar, G. Z. Naturforsch B., Chem. Sci. 1988, 43, 599.
32. 6. See Adams in reference 5a. DMF at 120°C has also been used: Holm, R. H.; Stack. T. D. P. J. Am. Chem. Soc. 1988, 110, 2484.
33. 7. Murahashi, S.-I.; Yamamura, M.; Yanagisawa, K.-I.; Mita, N.; Kondo. K. J. Org. Chem. 1979, 44, 2408. Rane, A. M.; Miranda, E. I.; Soderquist. J. A. Tetrahedron Lett. 1994, 3225. With vinyl triflates: Martinez, A. G.; Barcina, J. O.; de Fresno Cerezo, A.; Subramanian, L. R. Synlett 1994, 561.
34. 7. Murahashi, S.-I.; Yamamura, M.; Yanagisawa, K.-I.; Mita, N.; Kondo. K. J. Org. Chem. 1979, 44, 2408. Rane, A. M.; Miranda, E. I.; Soderquist. J. A. Tetrahedron Lett. 1994, 3225. With vinyl triflates: Martinez, A. G.; Barcina, J. O.; de Fresno Cerezo, A.; Subramanian, L. R. Synlett 1994, 561.
35. 7. Murahashi, S.-I.; Yamamura, M.; Yanagisawa, K.-I.; Mita, N.; Kondo. K. J. Org. Chem. 1979, 44, 2408. Rane, A. M.; Miranda, E. I.; Soderquist. J. A. Tetrahedron Lett. 1994, 3225. With vinyl triflates: Martinez, A. G.; Barcina, J. O.; de Fresno Cerezo, A.; Subramanian, L. R. Synlett 1994, 561.
36. 8. Kosugi, M.; Shimizu, T.; Migita, T. Chem. Lett. 1978, 13. Migita, T.; Shimizu, T.; Asami, Y.; Shiobara, J.-I.; Kato, Y.; Kosugi, M. Bull. Chem. Soc. Jpn 1980, 53, 1385. Kosugi, M.; Ogata, T.; Terada, M.; Sano, H.; Migita. T. Bull. Chem. Soc. Jpn 1985, 58, 3657. See Soderquist in ref. 7.
37. 8. Kosugi, M.; Shimizu, T.; Migita, T. Chem. Lett. 1978, 13. Migita, T.; Shimizu, T.; Asami, Y.; Shiobara, J.-I.; Kato, Y.; Kosugi, M. Bull. Chem. Soc. Jpn 1980, 53, 1385. Kosugi, M.; Ogata, T.; Terada, M.; Sano, H.; Migita. T. Bull. Chem. Soc. Jpn 1985, 58, 3657. See Soderquist in ref. 7.
38. 8. Kosugi, M.; Shimizu, T.; Migita, T. Chem. Lett. 1978, 13. Migita, T.; Shimizu, T.; Asami, Y.; Shiobara, J.-I.; Kato, Y.; Kosugi, M. Bull. Chem. Soc. Jpn 1980, 53, 1385. Kosugi, M.; Ogata, T.; Terada, M.; Sano, H.; Migita. T. Bull. Chem. Soc. Jpn 1985, 58, 3657. See Soderquist in ref. 7.
39. 9. Hugues, G. K., Thompson, E.O.P. J. Proc. Roy. Soc. N.S. Wales 1949, 83, 269. Adams, R., Ferretti, A., J. Am. Chem. Soc. 1959, 4939.
40. 9. Hugues, G. K., Thompson, E.O.P. J. Proc. Roy. Soc. N.S. Wales 1949, 83, 269. Adams, R., Ferretti, A., J. Am. Chem. Soc. 1959, 4939.
41. 10. Testaferri, L.; Tingoli, M.; Tiecco, M. Tetrahedron Lett. 1980, 3099. Testaferri, L., Tiecco, M., Tingoli, M., Chianelli, D.; Montanucci, M. Synthesis 1983, 751. NMP/nPrSNa: see Shaw in ref. 4a. Other S-demethylations: Young. R. N.; Gauthier, J. Y.; Coombs. W. Tetrahedron Lett. 1984, 1753. Lavanish, J. M. Tetrahedron Lett. 1973, 3847.
42. 10. Testaferri, L.; Tingoli, M.; Tiecco, M. Tetrahedron Lett. 1980, 3099. Testaferri, L., Tiecco, M., Tingoli, M., Chianelli, D.; Montanucci, M. Synthesis 1983, 751. NMP/nPrSNa: see Shaw in ref. 4a. Other S-demethylations: Young. R. N.; Gauthier, J. Y.; Coombs. W. Tetrahedron Lett. 1984, 1753. Lavanish, J. M. Tetrahedron Lett. 1973, 3847.
43. 10. Testaferri, L.; Tingoli, M.; Tiecco, M. Tetrahedron Lett. 1980, 3099. Testaferri, L., Tiecco, M., Tingoli, M., Chianelli, D.; Montanucci, M. Synthesis 1983, 751. NMP/nPrSNa: see Shaw in ref. 4a. Other S-demethylations: Young. R. N.; Gauthier, J. Y.; Coombs. W. Tetrahedron Lett. 1984, 1753. Lavanish, J. M. Tetrahedron Lett. 1973, 3847.
44. 10. Testaferri, L.; Tingoli, M.; Tiecco, M. Tetrahedron Lett. 1980, 3099. Testaferri, L., Tiecco, M., Tingoli, M., Chianelli, D.; Montanucci, M. Synthesis 1983, 751. NMP/nPrSNa: see Shaw in ref. 4a. Other S-demethylations: Young. R. N.; Gauthier, J. Y.; Coombs. W. Tetrahedron Lett. 1984, 1753. Lavanish, J. M. Tetrahedron Lett. 1973, 3847.
45. 11. Recrystallized from boiling EtOH or AcOH: BrPhSPhSMe: 94% yield; BrPhSPhSPhSMe: 62% yield