Tetrathiafulvalene: A convenient large-scale (20 g) synthesis

Synthesis

Volumn , Issue 4, 1997, Pages 407-409

  Moore, Adrian J ^a   Bryce, Martin R ^a  

^a DURHAM UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOSULFUR DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0030950056     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1209     Document Type: Article

References (23)

1. Wudl, F.; Smith, G. M.; Hufnagel, E. J. J. Chem. Soc., Chem. Commun. 1970, 1453. Hünig, S.; Kiesslich, G.; Scheutzow, D.; Zahradnik, R.; Carsky, P. Int. J. Sulfur Chem. Part C 1971, 109.
2. Wudl, F.; Smith, G. M.; Hufnagel, E. J. J. Chem. Soc., Chem. Commun. 1970, 1453. Hünig, S.; Kiesslich, G.; Scheutzow, D.; Zahradnik, R.; Carsky, P. Int. J. Sulfur Chem. Part C 1971, 109.
3. Bryce, M. R. Chem. Soc. Rev. 1991, 20, 355. 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: New Jersey, 1992. Ferraro, J. R.; Williams, J. M. Introduction to Synthetic Electrical Conductors; Academic Press: London, 1987. J. Mater. Chem. Special Issue on Molecular Conductors, 1995, 5, 1469-1760.
4. Bryce, M. R. Chem. Soc. Rev. 1991, 20, 355. 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: New Jersey, 1992. Ferraro, J. R.; Williams, J. M. Introduction to Synthetic Electrical Conductors; Academic Press: London, 1987. J. Mater. Chem. Special Issue on Molecular Conductors, 1995, 5, 1469-1760.
5. Bryce, M. R. Chem. Soc. Rev. 1991, 20, 355. 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: New Jersey, 1992. Ferraro, J. R.; Williams, J. M. Introduction to Synthetic Electrical Conductors; Academic Press: London, 1987. J. Mater. Chem. Special Issue on Molecular Conductors, 1995, 5, 1469-1760.
6. Bryce, M. R. Chem. Soc. Rev. 1991, 20, 355. 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: New Jersey, 1992. Ferraro, J. R.; Williams, J. M. Introduction to Synthetic Electrical Conductors; Academic Press: London, 1987. J. Mater. Chem. Special Issue on Molecular Conductors, 1995, 5, 1469-1760.
7. Jørgensen, T.; Hansen, T. K.; Becher, J. Chem. Soc. Rev. 1994, 41.
8. Garín, J. Adv. Heterocycl. Chem. 1995, 62, 249.
9. Murphy, J. A.; Roome, S. J. J. Chem. Soc., Perkin Trans. 1 1995, 1349 and references therein.
10. Garín, J.; Orduna, J.; Uriel, S.; Moore, A. J.; Bryce, M. R.; Wegener, S.; Yufit, D. S.; Howard, J. A. K. Synthesis 1994, 489, and references therein.
11. Melby, L. R.; Hartzler, H. D.; Sheppard, W. A. J. Org. Chem. 1974, 39, 2456.
12. Wudl, F.; Kaplan, M. L.; Hufnagel, E. J.; Southwick, E. W. J. Org. Chem. 1974, 39, 3608.
13. Guziec, F. S.; Russo, J. M.; Torres, F. F; Long, G. C.; Tellez, M. R. J. Chem. Soc., Perkin Trans. 1 1989, 1068.
14. Lerstrup, K.; Johannsen, I.; Jørgensen, M. Synth. Met. 1989, 27, B9.
15. Mora, H.; Fahre, J.-M.; Giral, L.; Montginoul, C. Bull. Soc. Chim. Belg. 1992, 101, 137.
16. Reviews: Krief, A. Tetrahedron 1986, 42, 1209. Schukat, G.; Richter, A. M.; Fanghänel, E. Sulfur Reports 1987, 7, 155.
17. Reviews: Krief, A. Tetrahedron 1986, 42, 1209. Schukat, G.; Richter, A. M.; Fanghänel, E. Sulfur Reports 1987, 7, 155.
18. The current price of TTF is £53.10 per gram (e.g., Aldrich catalogue, 1996-7).
19. After completion of this work, we were informed by Professor R. Elsenbaumer (University of Texas at Arlington) that a synthesis of TTF has been developed in his laboratory, starting from (Z)-1,2-dichloroethylene and the sodium salt derived from 4,5-bis(benzoylthio)-1,3-dithiole-2-thione. (R. L. Elsenbaumer, personal discussions, August 1996). We note that the current price of (Z)-1,2-dichloroethylene is £38.40 for 10 g (e.g., Aldrich catalogue 1996-7).
20. Fourmigué, M.; Krebs, F. C.; Larsen, J. Synthesis 1993, 509.
21. Moore, A. J.; Bryce, M. R. J. Chem. Soc., Perkin Trans, 1 1991, 157.
22. For examples, see references in: Bryce, M. R.; Moore, A. J.; Tanner, B. K.; Whitehead, R.; Clegg, W.; Gerson, F.; Lamprecht, A.; Pfenninger, S. Chem. Mater. 1996, 5, 1481. Misaki, Y; Ohta, T; Higuchi, N.; Fujiwara, H.; Yamabe, T; Mori, T; Mori, H.; Tanaka, S. J. Mater. Chem. 1995, 5, 1571.
23. For examples, see references in: Bryce, M. R.; Moore, A. J.; Tanner, B. K.; Whitehead, R.; Clegg, W.; Gerson, F.; Lamprecht, A.; Pfenninger, S. Chem. Mater. 1996, 5, 1481. Misaki, Y; Ohta, T; Higuchi, N.; Fujiwara, H.; Yamabe, T; Mori, T; Mori, H.; Tanaka, S. J. Mater. Chem. 1995, 5, 1571.