α-Linked Bifuran and α,α′-Linked Tricycles Containing Furan and/or Thiophene. EPR Investigations and Electrochemical Behavior

Journal of Organic Chemistry

Volumn 63, Issue 16, 1998, Pages 5324-5331

  Fajari Ll ^a   Brillas, E ^b   Aleman C ^c   Julia L ^a  

^a Ctr d'Investigacio i D   (Spain)

^b UNIVERSITY OF BARCELONA   (Spain)

^c UNIVERSITAT POLITÈCNICA DE CATALUNYA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001083244     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9719618     Document Type: Article

References (53)

1. (a) Handbook of Conducting Polymers; Skotheim, T. A., Ed.; Marcel Dekker: New York, 1986; Vols, 1 and 2.
2. (b) Conjugated Polymers and Related Materials; Salaneck, W. R., Lundström, I., Ranky, B., Eds; Oxford University Press: Oxford, 1993.
3. Proceedings of the International Conference of Science and Technology of Synthetic Metals (ICSM'94); Seoul, Korea, 1994; published in Synth. Met. 1995, 69.
4. Proceedings of the International Conference of Science and Technology of Synthetic Metals (ICSM'94); Seoul, Korea, 1994; published in Synth. Met. 1995, 69.
5. (a) Roncali, J. Chem. Rev. 1992, 92, 711.
6. (b) Roncali, J. Chem. Rev. 1997, 37, 173.
7. Frommer, J. E.; Chance, R. R. In Electrical and Electronic Properties of Polymers: A State-of-the-Art Compendium, Kroschwitz, J. I., Ed; John Wiley: New York, 1988; p 56.
8. (a) Davies, A. G.; Juliá, L.; Yazdi, S. N. J. Chem. Soc., Chem. Commun. 1987, 929.
9. (b) Davies, A. G.; Juliá, L.; Yazdi, S. N. J. Chem. Soc., Perkin Trans. 2 1989, 239.
10. (c) Alemán, C.; Brillas, E.; Davies, A. G.; Fajarí, Ll.; Giró, D.; Juliá, L., Pérez; J. J.; Rius, J. J. Org. Chem. 1993, 58, 3091.
11. (d) Giménez, E.; Carilla, J.; Fajarí, Ll.; Alemán, C.; Juliá, L. J. Org. Chem. 1994, 59, 4630.
12. (e) Alemán, C.; Juliá, L. J. Phys. Chem. 1996, 100, 1524.
13. (f) Alemán, C. Macromol. Theory Simul. 1997, 6, 233.
14. (g) Alemán, C.; Juliá, L. J. Phys. Chem. 1996, 100, 14661.
15. (h) Tormo, J.; Moreno, F. J.; Ruiz, J.; Fajarí, Ll.; Juliá, L. J. Org. Chem. 1997, 62, 878.
16. (i) Barbosa, F.; Eberson, L.; Gescheidt, G.; Gronowitz, S.; Hörnfeldt, A.-B.; Juliá, L.; Persson, O. Acta Chem. Scand., in press.
17. Davies, A. G. Chem. Soc. Rev. 1993, 299.
18. (a) Avila, D. N.; Davies, A. G. J. Chem. Soc., Faraday Trans. 1990, 86, 3243.
19. (b) Davies, A. G.; Schiesser, C. H. J. Organomet. Chem. 1990, 389, 301.
20. (c) Avila, D. N.; Davies, A. G. J. Chem. Soc., Perkin Trans. 2 1991, 1111.
21. To know the useful properties of HFP as a good solvent for radical cations, see: Eberson, L.; Hartshorn, M. P.; Persson, O.; Radner, F. J. Chem. Soc., Chem. Commun. 1996, 2105.
22. (a) Alberti A.; Favaretto, L.; Seconi, G. J. Chem. Soc., Perkin Trans. 2 1990, 931.
23. (b) Zinger, B.; Mann, K. R.; Hill, M. G.; Miller, L. L. Chem. Mater, 1992, 4, 1113.
24. (c) Kirste, B.; Tian, P.; Kossmehl, G.; Engelmann, G.; Jugelt, W. Magn. Reson. Chem. 1995, 33, 70.
25. (d) Engelmann, G.; Stösser, R.; Kossmehl, G.; Jugelt, W.; Welzel, H.-P. J. Chem. Soc., Perkin Trans. 2 1996, 2015.
26. (a) Zhou, Z-h.; Maruyama, T.; Kanbara, T.; Ikeda, T.; Ichimura, K.; Yamamoto, T.; Tokuda, K J. Chem. Soc., Chem. Commun. 1991, 1210.
27. (b) Tamao, K; Yamaguchi, S.; Shiozaki, M.; Nakagawa, Y.; Ito, Y. J. Am. Chem. Soc. 1992, 114, 5867.
28. (c) Tamao, K.; Yamaguchi, S.; Ito, Y. J. Chem. Soc., Chem. Commun. 1994, 229.
29. (d) Tamao, K.; Ohno, S.; Yamaguchi, S. J. Chem. Soc., Chem. Commun. 1996, 1873. Joshi, M. V.; Hemler, C.; Cava, M. P.; Cain, J. L.; Bakker, M. G.; McKinley, A. J.; Metzger, R. M. J. Chem. Soc., Perkin Trans. 2 1993, 1081.
30. (d) Tamao, K.; Ohno, S.; Yamaguchi, S. J. Chem. Soc., Chem. Commun. 1996, 1873. Joshi, M. V.; Hemler, C.; Cava, M. P.; Cain, J. L.; Bakker, M. G.; McKinley, A. J.; Metzger, R. M. J. Chem. Soc., Perkin Trans. 2 1993, 1081.
31. Alemán, C.; Domingo, V. M.; Fajarí, Ll.; Juliá, L.; Karpfen, A. J. Org. Chem. 1998, 63, 1041.
32. Armour, M.; Davies, A. G.; Upadhyay, J.; Wassermann, A. J. Polym. Sci., Part A-1 1967, 5, 1527, Tourillon, G.; Garnier, F. J. Electroanal. Chem. 1982, 135, 173. Ohsawa, T.; Kaneto, K.; Yoshino, K. Jpn. J. Appl. Phys. 1984, 23, L663. Nessakh, B.; Kotkowska-Machnik, Z.; Tedjar, F. J. Electroanal. Chem. 1990, 269, 263. Tedjar, F. Eur. Polym. J. 1985, 21, 317. Zotti, G.; Schiavon, G.; Comisso, N. Synth. Met. 1990, 36, 337.
33. Armour, M.; Davies, A. G.; Upadhyay, J.; Wassermann, A. J. Polym. Sci., Part A-1 1967, 5, 1527, Tourillon, G.; Garnier, F. J. Electroanal. Chem. 1982, 135, 173. Ohsawa, T.; Kaneto, K.; Yoshino, K. Jpn. J. Appl. Phys. 1984, 23, L663. Nessakh, B.; Kotkowska-Machnik, Z.; Tedjar, F. J. Electroanal. Chem. 1990, 269, 263. Tedjar, F. Eur. Polym. J. 1985, 21, 317. Zotti, G.; Schiavon, G.; Comisso, N. Synth. Met. 1990, 36, 337.
34. Armour, M.; Davies, A. G.; Upadhyay, J.; Wassermann, A. J. Polym. Sci., Part A-1 1967, 5, 1527, Tourillon, G.; Garnier, F. J. Electroanal. Chem. 1982, 135, 173. Ohsawa, T.; Kaneto, K.; Yoshino, K. Jpn. J. Appl. Phys. 1984, 23, L663. Nessakh, B.; Kotkowska-Machnik, Z.; Tedjar, F. J. Electroanal. Chem. 1990, 269, 263. Tedjar, F. Eur. Polym. J. 1985, 21, 317. Zotti, G.; Schiavon, G.; Comisso, N. Synth. Met. 1990, 36, 337.
35. Armour, M.; Davies, A. G.; Upadhyay, J.; Wassermann, A. J. Polym. Sci., Part A-1 1967, 5, 1527, Tourillon, G.; Garnier, F. J. Electroanal. Chem. 1982, 135, 173. Ohsawa, T.; Kaneto, K.; Yoshino, K. Jpn. J. Appl. Phys. 1984, 23, L663. Nessakh, B.; Kotkowska-Machnik, Z.; Tedjar, F. J. Electroanal. Chem. 1990, 269, 263. Tedjar, F. Eur. Polym. J. 1985, 21, 317. Zotti, G.; Schiavon, G.; Comisso, N. Synth. Met. 1990, 36, 337.
36. Armour, M.; Davies, A. G.; Upadhyay, J.; Wassermann, A. J. Polym. Sci., Part A-1 1967, 5, 1527, Tourillon, G.; Garnier, F. J. Electroanal. Chem. 1982, 135, 173. Ohsawa, T.; Kaneto, K.; Yoshino, K. Jpn. J. Appl. Phys. 1984, 23, L663. Nessakh, B.; Kotkowska-Machnik, Z.; Tedjar, F. J. Electroanal. Chem. 1990, 269, 263. Tedjar, F. Eur. Polym. J. 1985, 21, 317. Zotti, G.; Schiavon, G.; Comisso, N. Synth. Met. 1990, 36, 337.
37. Armour, M.; Davies, A. G.; Upadhyay, J.; Wassermann, A. J. Polym. Sci., Part A-1 1967, 5, 1527, Tourillon, G.; Garnier, F. J. Electroanal. Chem. 1982, 135, 173. Ohsawa, T.; Kaneto, K.; Yoshino, K. Jpn. J. Appl. Phys. 1984, 23, L663. Nessakh, B.; Kotkowska-Machnik, Z.; Tedjar, F. J. Electroanal. Chem. 1990, 269, 263. Tedjar, F. Eur. Polym. J. 1985, 21, 317. Zotti, G.; Schiavon, G.; Comisso, N. Synth. Met. 1990, 36, 337.
38. Glenis, S.; Benz, M.; LeGoff, E.; Schindler, J. L.; Kannewurf, C. R.; Kanatzidis, M. G. J. Am. Chem. Soc. 1993, 115, 12519. González-Tejera, M. J.; Carrillo, I.; Hernández-Fuentes, I. Synth. Met. 1995, 73, 135.
39. Glenis, S.; Benz, M.; LeGoff, E.; Schindler, J. L.; Kannewurf, C. R.; Kanatzidis, M. G. J. Am. Chem. Soc. 1993, 115, 12519. González-Tejera, M. J.; Carrillo, I.; Hernández-Fuentes, I. Synth. Met. 1995, 73, 135.
40. Leung, W.-Y.; LeGoff, E. Synth. Commun. 1989, 19, 787.
41. El-Hajj, T.; Martin, J.-C.; Descotes, G. J. Heterocycl. Chem. 1983, 20, 233.
42. Wu, C.-G.; Marcy, H. O.; De Groot, D. L.; Schindler, J. L.; Kannewurf, C. R.; Leung, W.-Y.; Benz, M.; LeGoff, E.; Kanatzidis, M. G. Synth. Met. 1991, 41-43, 797.
43. Davies A. G.; McGuchan, C. Organometallics 1991, 10, 329.
44. 22
45. Dewar, M. J. S.; Thiel, W. J. Am. Chem. Soc. 1977, 99, 4899.
46. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B, G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. GAUSSIAN94, Revision E.1; Gaussian, Inc.: Pittsburgh, PA, 1995.
47. McConnell, H. M.; Chesnut, D. B. J. Chem. Phys. 1958, 28, 107.
48. Fundamentals of Electrochemical Analysis; Galus, Z., Ed.; Horwood: Chichester, 1976; Chapters 7 and 9.
49. Organic Electrochemistry. An Introduction and a Guide; 3rd ed.; Lund, H., Baizer, M. M., Eds.; Marcel Dekker: New York, 1991; Chapters 2 and 3.
50. Cunningham, D. D.; Laguren-Davidson, L.; Mark, H. B.; Van Pham, Ch.; Zimmer, H. J. Chem. Soc., Chem. Commun. 1987, 1021; Galal, A.; Lewis, E. T.; Ataman, O. Y.; Zimmer H.; Mark Jr., H. B. J. Polym. Sci., Polym. Chem. 1989, 27, 1891.
51. Cunningham, D. D.; Laguren-Davidson, L.; Mark, H. B.; Van Pham, Ch.; Zimmer, H. J. Chem. Soc., Chem. Commun. 1987, 1021; Galal, A.; Lewis, E. T.; Ataman, O. Y.; Zimmer H.; Mark Jr., H. B. J. Polym. Sci., Polym. Chem. 1989, 27, 1891.
52. Arco, M. J.; Trammell, M. H.; White, J. D. J. Org. Chem. 1976, 41, 2075.
53. Eachern, A. M.; Soucy, Ch.; Leitch, L. C.; Arnason, J. T.; Morand, P. Tetrahedron 1988, 44, 2403.