A new promising π-donor of the tetrathiafulvalene series: bis(2,3-dithiabutane-1,4-diyl)tetrathiafulvalene, the symmetrical outer S-position isomer of BEDT-TTF
(Note: The full text of this document is currently only available in the PDF Version )
C. Durand, P. Hudhomme, G. Duguay, C. Durand, M. Jubault and A. Gorgues
Abstract
New functionalities are introduced into the 2-(thi)oxo-1,3-dithiole system and applied to the synthesis of the title compound.
References
G. Schukat and E. Fanghänel, Sulfur Rep., 1993, 14, 245 Search PubMed; J. Garin, Adv. Heterocycl. Chem., 1995, 62, 249 CAS and references cited therein.
(a) J. M. Williams,
J. R. Ferraro,
R. J. Thorn,
K. D. Carlson,
U. Geiser,
H. H. Wang,
A. M. Kini and
M. H. Whangbo,
Organic Superconductors (including fullerenes),
Prentice Hall,
Englewood Cliffs, New Jersey,
1992 Search PubMed;
(b) J. P. Farges,
Organic conductors. Fundamentals and applications,
Marcel Dekker,
New York,
1994 Search PubMed.
k-(BEDT-TTF)2Cu[N(CN)2]X (Tc= 11.6 K at ambient pressure for X = Br and 12.8 K at 0.3 kbar for X = Cl): A. M. Kini, U. Geiser, H. H. Wang, K. D. Carlson, J. M. Williams, W. K. Kwok, K. G. Vandervoort, J. E. Thompson, D. L. Stupka, D. Jung and M. H. Whangbo, Inorg. Chem., 1990, 29, 2555 Search PubMed; J. M. Williams, A. M. Kini, H. H. Wang, K. D. Carlson, U. Geiser, L. K. Montgomery, G. J. Pyrka, D. M. Watkins, J. M. Kommers, S. J. Boryschuk, A. V. Strieby Crouch, W. K. Kwok and M. H. Whangbo, Inorg. Chem., 1990, 29, 3272 CrossRefCAS.
J. M. Williams, Prog. Inorg. Chem., 1985, 33, 183 CAS; L. Binet, J. M. Fabre and J. Becher, Synthesis, 1997, 26 CrossRefCAS.
J. J. Novoa, M. C. Rovira, C. Rovira, J. Veciana and J. Tarrés, Adv. Mater., 1995, 7, 233 CAS; M. C. Rovira, J. J. Novoa, J. Tarrés, C. Rovira, J. Veciana, S. Yang, D. O. Cowan and E. Canadell, Adv. Mater., 1995, 7, 1023 CAS.
P. Hudhomme, P. Blanchard, M. Sallé, S. Le Moustarder, A. Riou, M. Jubault, A. Gorgues and G. Duguay, Angew. Chem., Int. Ed. Engl., 1997, 36, 878 CrossRefCAS.
H. Gotthardt,
Comprehensive Heterocyclic Chemistry,
ed. A. R. Katritzky,
Pergamon,
Oxford,
1984, vol. 6,
p. 813 Search PubMed.
M. A. Fox and H. Pan, J. Org. Chem., 1994, 59, 6519 CrossRefCAS.
R. P. Volante, Tetrahedron Lett., 1981, 22, 3119 CrossRefCAS; K. C. Nicolaou and A. L. Smith, Phosphorus Sulfur Silicon Relat. Elem., 1993, 74, 47 CAS.
R. F. Abdulla and R. S. Brinkmeyer, Tetrahedron, 1979, 35, 1675 CrossRefCAS.
This result has to be compared with a similar reaction (CBr4, PPh3) very
recently described for 7a(70% yield); P. J. Skabara and K. Müllen, Synth. Met., 1997, 84, 345 Search PubMed.
R. M. Renner and G. R. Burns, Tetrahedron Lett., 1994, 35, 269 CrossRefCAS.
R. Gasiorowski, T. Jorgensen, J. Moller, T. K. Hansen, M. Pietraszkiewicz and J. Becher, Adv. Mater., 1992, 4, 568 CAS.
M. Narita and C. U. Pittman, Synthesis, 1976, 489 CrossRefCAS; A. Krief, Tetrahedron, 1986, 42, 1209 CrossRefCAS and references cited therein.
G. Le Coustumer and Y. Mollier, J. Chem. Soc., Chem. Commun., 1980, 38 RSC.
An analogous desulfurization with P(OMe)3 was observed for thionolactone to afford corresponding lactone: S. Ayral-Kaloustian and W. C. Agosta, Synth. Commun., 1981, 11, 1011 Search PubMed.
We are investigating the possibility of accessing the unsymmetrical TTF from the phosphonate, easily obtained in 75% yield by classical reaction of 10 with NaI and P(OMe)3: A. J. Moore and M. R. Bryce, Synthesis, 1991, 26 Search PubMed.
Click here to see how this site uses Cookies. View our privacy policy here.