Tetraformyltetrathiafulvalene(TFTTF): Synthesis and some uses as a precursor of polyfunctionalised tetrathiafulvalenes

Journal of the Chemical Society - Series Chemical Communications

Volumn , Issue 8, 1983, Pages 405-406

  Gorgues, Alain ^a   Batail, Patrick ^a   Coq, André Le ^a  

^a UNIVERSITÉ DE RENNES 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049112587     PISSN: 00224936     EISSN: None     Source Type: Journal    
DOI: 10.1039/C39830000405     Document Type: Article

References (20)

1. For reviews, E. M. Engler, CHEMTECH., 1976, 6, 274;
2. For reviews, M. Narita and C. U. Pittman, Jr., Synthesis,1976, 489.
3. E. M. Engler, V. V. Patel, J. R. Andersen, R. R. Schumaker, and A. A. Fukushima, J. Am. Chem. Soc.,1978, 100, 3769, and references therein;
4. A. Mas, J. M. Fabre, E. Toreilles, L. Giral, and G. Brun, Tetrahedron Lett.,1977, 2579;
5. ‘The Physics and Chemistry of Low Dimensional Solids,’ ed. L. Alcacer, D. Reidel, Dordrecht, Holland, 1980.
6. F. Wudl and E. Aharon-Shalom, J. Am. Chem. Soc.,1982, 104, 1154;
7. K. Lerstrup, D. Talham, A. Bloch, T. Poehler, and D. Cowan, J. Chem. Soc., Chem. Commun.,1982, 336.
8. D. Jerome, A. Mazaud, M. Ribault, and K. Bechgaard, J. Phys. Lett.,1980, 41, L-95;
9. K. Bechgaard, K. Carneiro, F. B. Rasmussen, G. Rinsdorf, C. S. Jacobsen, H. J. Pedersen, and J. C. Scott, J. Am. Chem. Soc.,1981, 103, 2440;
10. D. Jerome, Mol. Cryst. Liq. Cryst.,1982, 79, 155;
11. D. Jerome, Conference Rennes, 22 Oct., 1981, and personal communication;
12. S. S. P. Parkin, F. Creuzet, M. Ribault, D. Jerome, K. Bechgaard, and J. M. Fabre, Mol. Cryst. Liq. Cryst.,1982, 79, 249.
13. Monoformyltetrathiafulvalene (and small amounts of di- formyltetrathiafulvalene) have previously been prepared (30% yield from TTF) and transformed into the corresponding vinyltetrathiafulvalene through a Wittig reaction: D. C. Green and R. W. Allen, J. Chem. Soc., Chem. Commun., 1978, 832;
14. D. C. Green, J. Org. Chem.,1979, 44, 1476.
15. A. Gorgues and A. Le Coq, Tetrahedron Lett.,1979, 4825 and 4829;
16. A. Gorgues and A. Le Coq J. Chem. Soc., Chem. Commun.,1979, 767.
17. G. Le Coustumer and Y. Mollier, J. Chem. Soc., Chem. Commun.,1980, 38. As previously noticed in other experiments by H. Alper and H. N. Park, J. Org. Chem.,1977, 42, 3522 we observed (thin layer chromatography) the formation of transient organometallic species which thermally evolve into (5).
18. For the formolysis of acetals, see A. Gorgues, Bull. Soc. Chim. Fr.,1974, 529.
19. Generated by treatment of Ph3PCHMe2I, G. Wittig and H. Wittenberg, Liebigs Ann. Chem.,1957, 606, 1, with (Me3Si)2NLi in tetrahydrofuran.
20. Temperature dependent conductivity and thermo-power measurements showed this material to be a semiconductor with a rather small band gap (0.06 eV); electrons are the main carriers (S= –54 VK'1 at 300 K), P. Batail and R. L. Greene, unpublished results. This was further confirmed by i.r. spectroscopy which gives a gap of ca.700 cm-1; A. Girlando, personal communication.