A straightforward access to mono- and bis(pyrrolo)tetrathiafulvalenes

Synthesis

Volumn , Issue 17, 2006, Pages 2815-2817

  Balandier, Jean Yves ^a   Belyasmine, Ahmed ^a   Sallé, Marc ^a  

^a UNIVERSITÉ D'ANGERS   (France)

Author keywords

4,4 diethoxybut 2 ynal; Acetals; Pyrroles; Ring closure; Tetrathiafulvalene

Indexed keywords

ACETAL RESINS; SYNTHESIS (CHEMICAL);

4,4-DIETHOXYBUT-2-YNAL; ACETALS; PYRROLES; RING CLOSURE; TETRATHIAFULVALENE;

ORGANIC COMPOUNDS;

BIS(PYRROLO)TETRATHIAFULVALENE DERIVATIVE; MONO(PYRROLO)TETRATHIAFULVALENE DERIVATIVE; TETRATHIAFULVALENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; MASS SPECTROMETRY; PURIFICATION; SYNTHESIS;

EID: 33748806845     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-942520     Document Type: Article

References (28)

1. Molecular Conductors (thematic issue), Chem. Rev; Batail, P., Ed.; 2004, 104, issue 11.
2. (a) Segura, J. L.; Martín, N. Angew. Chem. Int. Ed. 2001, 40, 1372.
3. (b) Brøndstedt Nielsen, M.; Lomholt, C.; Becher, J. Chem. Soc. Rev. 2000, 29, 143.
4. (c) Jeppesen, J. O.; Becher, J. Eur. J. Org. Chem. 2003, 3245.
5. (a) Bendikov, M.; Wudl, F.; Perepichka, D. F. Chem. Rev. 2004, 104, 4891.
6. (b) Yamada, J. I.; Akutsu, H.; Nishikawa, H.; Kikuchi, K. Chem. Rev. 2004, 104, 5057.
7. (c) Iyoda, M.; Hasegawa, M.; Miyake, Y. Chem. Rev. 2004, 104, 5085.
8. (d) Jeppesen, J. O.; Brøndsted Nielsen, M.; Becher, J. Chem. Rev. 2004, 104, 5115.
9. (e) Fahre, J. M. Chem. Rev. 2004, 104, 5133.
10. (f) Gorgues, A.; Hudhomme, P.; Sallé, M. Chem. Rev. 2004, 104, 5151.
11. (g) Lorcy, D.; Bellec, N. Chem. Rev. 2004, 104, 5185.
12. (h) Frère, P.; Skabara, P. Chem. Soc. Rev. 2005, 34, 69.
13. (i) Otsubo, T. Bull Chem. Soc. Jpn. 2004, 77, 43.
14. (a) Jeppesen, J. O.; Takimiya, K.; Jensen, F.; Becher, J. Org. Lett. 1999, 1, 1291.
15. (b) Jeppesen, J. O.; Takimiya, K.; Jensen, F.; Brimert, T.; Nielsen, K.; Thorup, N.; Becher, J. J. Org. Chem. 2000, 65, 5794.
16. For very recent examples, see for instance: (a) Nygaard, S.; Laursen, B. W.; Flood, A. H.; Hansen, C. N.; Jeppesen, J. O.; Stoddart, J. F. Chem. Commun. 2006, 144.
17. (b) Jeppesen, J. O.; Nygaard, S.; Vignon, S. A.; Stoddart, J. F. Eur. J. Org. Chem. 2005, 196.
18. (c) Choi, J. W.; Flood, A. H.; Steuerman, D. W.; Nygaard, S.; Braunschweig, A. B.; Moonen, N. N. P.; Laursen, B. W.; Luo, Y.; DeIonno, E.; Peters, A. J.; Jeppesen, J. O.; Xu, K.; Stoddart, J. F.; Heath, J. R. Chem. Eur. J. 2006, 12, 261.
19. (a) Trippé, G.; Levillain, E.; Le Derf, F.; Gorgues, A.; Sallé, M.; Jeppesen, J. O.; Nielsen, K.; Becher, J. Org. Lett. 2002, 4, 2461.
20. (b) Nielsen, K. A.; Cho, W. S.; Jeppesen, J. O.; Lynch, V. M.; Becher, J.; Sessler, J. L. J. Am. Chem. Soc. 2004, 126, 16296.
21. (a) Yin, B.; Yang, Y.; Cong, Z.; Imafuku, K. Heterocycles 2004, 63, 1577.
22. (b) Li, H.; Lambert, C. Chem. Eur. J. 2006, 12, 1144.
23. Gorgues, A.; Stephan, D.; Belyasmine, A.; Khanous, A.; Le Coq, A. Tetrahedron 1990, 46, 2817.
24. Compound 2 is commercially available from Acros Organics.
25. Sallé, M.; Gorgues, A.; Jubault, M.; Boubekeur, K.; Batail, P. Tetrahedron 1992, 48, 3081.
26. Attempts to purify imine 4 by silica gel or alumina chromatography invariably led to a partial reverse reaction to the starting products.
27. Alternatively, compound 5 may be directly engaged in the following step without being chromatographed (no noticeable loss in the yield of 6). In fact, the purification of 5 by silica gel chromatography is accompanied by formation of compound 6.
28. We observed lower yields with longer times.