New versatile building blocks in tetrathiafulvalene (TTF) chemistry: 2,3-bis(bromomethyl) and tetrakis(bromomethyl)TTFs

Tetrahedron Letters

Volumn 40, Issue 15, 1999, Pages 2927-2930

  Hudhomme, P ^a   Liu, S G ^a   Kreher, D ^a   Cariou, M ^a   Gorgues, A ^a  

^a UNIVERSITÉ D'ANGERS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

2,3 BIS(BROMOMETHYL)TETRATHIOFULVALENE; TETRAKIS(BROMOMETHYL)TETRATHIOFULVALENE; TETRATHIAFULVALENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ELECTRON TRANSPORT; STRUCTURE ACTIVITY RELATION;

EID: 0033537994     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00325-1     Document Type: Article

References (26)

1. Jeppesen, J.O.; Takimiya, K.; Becher, J. Synthesis, 1999, in press.
2. 60 fused dyads : a) Boulle, C.; Rabreau, J.M.; Hudhomme, P.; Cariou, M.; Jubault, M.; Gorgues, A.; Orduna, J.; Garín, J. Tetrahedron Lett., 1997, 38, 3909-10;
3. b) Hudhomme, P.; Boulle, C.; Rabreau, J.M.; Cariou, M.; Jubault, M.; Gorgues, A. Synth. Met., 1998, 94, 73-75;
4. c) Gorgues, A.; Sallé, M.; Hudhomme, P.; Leriche, P.; Boulle, C.; Durand, C.; Le Derf, F.; Cariou, M.; Jubault, M.; Blanchard, P. Supramolecular Engineering of Synthetic Metallic Materials: Conductors and Magnets, Ed. Veciana, J. et al., NATO ASI Series, Kluwer Acad Pub, Dordrecht, 1999, 451-64.
5. a) Williams, J.M.; Ferraro, J.R.; Thorn, R.J.; Carlson, K.D.; Geiser, U.; Wang, H.H.; Kini, A.M.; Whangbo, M-H Organic Superconductors (Including Fullerenes), Prentice Hall : Englewood Cliffs, New Jersey, 1992;
6. b) Organic Conductors. Fundamentals and Applications, Farges, J.P.; Marcel Dekker Inc., New York, 1994.
7. a) Schukat, G.; Fanghänel, E. Sulfur Reports, 1993, 14, 245-390;
8. b) Garín, J. Adv. Heterocycl. Chem., 1995, 62, 249-304.
9. a) Veciana, J.; Rovira, C.; Cowan, D. Tetrahedron Lett., 1988, 29, 3467-70;
10. b) Rovira, C.; Santalo, N.; Veciana, J. Tetrahedron Lett., 1989, 30, 7249-52;
11. c) Llacay, J.; Mas, M.; Molins, E.; Veciana, J.; Powell, D.; Rovira, C. Chem. Commun., 1997, 659-60;
12. d) Llacay, J.; Veciana, J.; Vidal-Gancedo, J.; Bourdelande, J.L.; González-Moreno, R.; Rovira, C. J. Org. Chem., 1998, 63, 5201-10.
13. Belik, P.; Gügel, A.; Spickermann, J.; Müllen, K. Angew. Chem. Int. Ed. Engl., 1993, 32, 78-80.
14. Boulle, C.; Cariou, M.; Bainville, M.; Gorgues, A.; Hudhomme, P.; Orduna, J.; Garín, J. Tetrahedron Lett., 1997, 38, 81-84.
15. Blanchard, P.; Duguay, G.; Cousseau, J.; Sallé, M.; Jubault, M.; Gorgues, A.; Boubekeur, K.; Batail, P. Synth. Met., 1993, 55-57, 2113-17.
16. a) Sallé, M.; Gorgues, A.; Jubault, M.; Boubekeur, K.; Batail, P. Tetrahedron, 1992, 48, 3081-90;
17. b) Fox, M.A.; Pan, H. J. Org. Chem., 1994, 59, 6519-27.
18. Durand, C.; Hudhomme, P.; Duguay, G.; Jubault, M.; Gorgues, A. Chem. Commun., 1998, 361-62.
19. Giffard, M.; Alonso, P.; Garín, J; Gorgues, A ; Nguyen, T.P.; Richomme, P.; Robert, A.; Roncali, J.; Uriel, S. Adv. Mater., 1994, 6, 298-300.
20. Hsu, S.; Chiang, L. Synth. Met., 1988, 27, B651-656.
21. b : a) Blanchard, P. Thesis Angers-Nantes Universities, 20 Sept. 1994,
22. b) Hudhomme, P. unpublished results.
23. 4 M = 576.092 Calc. % C = 20.85, % H = 1.40, % S = 22.26, % Br = 55.49; Found % C = 21.01, % H = 1.55, % S = 21.73, % Br = 51.09.
24. 2O with 2-(hydroxymethyl)TTF to afford the trifluoroacetate leaving group has been described : Nozdryn, T.; Clémenceau, D.; Cousseau, J.; Morisson, V.; Gorgues, A.; Orduna, J.; Uriel, S.; Garín, J. Synth. Met., 1993, 55-57, 1768-71.
25. 2O with 2-(hydroxymethyl)TTF to afford the trifluoroacetate leaving group has been described : Nozdryn, T.; Clémenceau, D.; Cousseau, J.; Morisson, V.; Gorgues, A.; Orduna, J.; Uriel, S.; Garín, J. Synth. Met., 1993, 55-57, 1768-71.
26. Liu, S.G.; Hudhomme, P.; Cariou, M.; Mas, M.; Vidal-Gancedo, J.; Rovira, C.; Veciana, J.; Gorgues, A. unpublished results.