Abstract
Methods for the synthesis of 1,3-dithiole-2-thiones, based on [4+2] cycloaddition of the 1,3-dithiole-2,4,5-trithione oligomer to various unsaturated acyclic, carbocyclic, and heterocyclic compounds, are reviewed. Methods for the production of substituted tetrathiafulvalenes, which can be regarded as derivatives of bis(ethylenedithio)tetrathiafulvalene, from 1,3-dithiole-2-thiones synthesized by this method are described.
Similar content being viewed by others
References
Ya. Ya. Katsens and Ya. N. Kreitsberga, USSR Inventor’s Certificate 1428753; Byull. Izobr., 37 (1988).
O. Ya. Neiland, Ya. Ya. Katsens, and Ya. N. Kreitsberga, Zh. Org. Khim., 25, 658 (1989).
N. Svenstrup and J. Becher, Synthesis, 215 (1995).
J. C. Lodmell, W. C. Anderson, M. F. Hurley, and J. Q. Chambers, Anal. Chim. Acta, 129, 49 (1981).
V. Yu. Khodorkovskii, G. G. Pukitis, A. Ya. Puplovskii, A. S. Edzhinya, and O. Ya. Neiland, Khim. Geterotsikl. Soedin., 131 (1990).
H. Li, D. Zhang, Yu Xu, W. Xu, G. Yu, X. Li, and D. Zhu, Synth. Met., 123, 385 (2001).
H. Li, D. Zhang, B. Zhang, Y. Yao, W. Xu, D. Zhu, and Zh. Wang, J. Mater. Chem., 10, 2063 (2000).
R. Medne, J. Kacens, I. L. Kraupsha, and O. Neilands, Khim. Geterotsikl. Soedin., 1317 (1991).
A. I. Kotov, C. Faulmann, P. Cassoux, and E. V. Yagubskii, J. Org. Chem., 59, 2626 (1994).
G. G. Abashev, V. S. Russkikh, and E. V. Shklyaeva, Zh. Org. Khim., 31, 1705 (1995).
G. G. Abashev, E. V. Shklyaeva, and A. G. Tenishev, in: Prospects for Natural Sciences in the Western Urals, Collections of Papers of International Conference [in Russian], Perm (2001), Vol. 1, p. 8.
G. G. Abashev, E. V. Shklyaeva, V. S. Russkikh, and S. Krol, Mendeleev Commun., 157 (1997).
M. R. Bryce, A. K. Lay, A. S. Batsanov, and J. A. K. Howard, Tetrahedron Lett., 40, 801 (1999).
G. G. Abashev, E. V. Shklyaeva, K. Yu. Lebedev, A. N. Nedugov, S. N. Popov, and I. V. Osorgina, in: International Conference on the Chemistry of Heterocyclic Compounds, Dedicated to the Ninetieth Birthday of Prof. Aleksei Nikolaevich Kost [in Russian], Moscow State University, Moscow (2005), p. 99.
R. V. Pisarev, V. V. Kalashnikov, A. I. Kotov, and E. G. Yagubskii, Izv. Akad. Nauk. Ser. Khim., 775 (1996).
I. Hellberg, K. Balodis, M. Moge, P. Korall, and I.-U. Von-Schultz, J. Mater. Chem., 7, 31 (1997).
Ya. Yoshiro, T. Masaaki, and I. Kenichi, Mol. Cryst. Liq. Cryst., 380, 203 (2002).
H. Nishikawa, Database of Organic Conductors, http://www.ossc.kuchem.kyoto-u.ac.jp/database/1synt/TTFderivl.pdf.
P. Leriche, A. Gorgues, M. Jubault, J. Becher, S. Uriel, J. Orduna, and J. Garin, Synth. Met., 70, 1143 (1995).
Ph. Leriche, A. Gorgues, M. Jubault, J. Becher, J. Orduna, and J. Garin, Tetrahedron Lett., 36, 1275 (1995).
R. Berridge, I. M. Serebryakov, P. J. Skabara, E. Orti, R. Viruels, R. Pou-Amerigo, S. J. Coles, and M. B. Hursthouse, J. Mater. Chem., 14, 2822 (2004).
A. Gorgues, P. Hudhomme, and M. Salle, Chem. Rev., 104, 5551 (2004).
J. P. Parakka, A. M. Kini, and J. M. Williams, Tetrahedron Lett., 37, 8085 (1996).
J. P. Parakka, A. M. Kini, and J. M. Williams, Synth. Met., 86, 805 (1997).
M. R. Bryce, A. K. Lay, A. Chesney, A. S. Batsanov, J. A. K. Howard, U. Buser, F. Gerson, and P. Merstetter, J. Chem. Soc. Perkin Trans. 2, 755 (1999).
R. A. Bissell, N. Boden, R. I. Bushby, C. W. G. Fishwick, E. Holland, B. Movaghar, and G. Ungar, Chem. Commun., 113 (1998).
V. Y. Khodorkovsky, J. Y. Becker, and J. Bernstein, Synth. Met., 56, 1931 (1993).
V. Y. Khodorkovsky, J. Y. Becker, and J. Bernstein, Synthesis, 1071 (1992).
D.-Y. Noh, H.-J. Lee, J. Hong, and A. E. Underhill, Tetrahedron Lett., 37, 7603 (1996).
H.-J. Lee and D.-Y. Noh, Bull. Korean Chem. Soc., 19, 340 (1998).
P. J. Skabara, I. M. Serebryakov, D. M. Roberts, I. F. Perepichka, S. J. Coles, and M. B. Hurthouse, J. Org. Chem., 64, 6418 (1999).
R. Andreu, J. Garin, J. Orduna, and J. M. Royo, Tetrahedron Lett., 41, 5207 (2000).
R. L. Meline and R. L. Elsenbaumer, Synthesis, 617 (1997).
J. D. Wallis and J.-P. Griffiths, J. Mater. Chem., 15, 347 (2005).
J.-P. Griffiths, R. J. Browan, A. Arola Arnal, G. Appleby, and J. D. Wallis, J. Phys. IV Fr., 114, 487 (2004).
A. M. Kini, J. P. Parakka, Urs Geiser, H.-H. Wang, F. Rivas, E. DiNino, S. Thomas, J. D. Dudek, and J. M. Williams, J. Mater. Chem., 9, 883 (1999).
Sh. Kimura, Sh. Hanazato, H. Kurai, T. Mori, Y. Misaki, and K. Tanaka, Tetrahedron Lett., 42, 5729 (2001).
J.-P. Griffiths, H. Nie, R. J. Brown, P. Day, and J. D. Wallis, Org. Biomol. Chem., 3, 2155 (2005).
Wei Xu, D. Zhang, H. Li, and D. Zhu, J. Mater. Chem., 9, 1245 (1999).
D. Zhang, W. Xu, Ch. Jia, H. Li, and D. Zhu, ARKIVOC, ii, 165 (2003).
H.-J. Lee and D.-Y. Noh, J. Mater. Chem., 10, 2167 (2000).
G. G. Abashev, E. V. Shklyaeva, V. S. Russkikh, and S. Krol, Mendeleev Commun., 155 (1997).
Author information
Authors and Affiliations
Additional information
Dedicated to the memory of Professor O. Neilands.
__________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 483–502, April, 2006.
Rights and permissions
About this article
Cite this article
Abashev, G.G., Shklyaeva, E.V. Synthesis of 1,3-dithiole-2-thiones and tetrathiafulvalenes using oligo-(1,3-dithiole-2,4,5-trithione). (Review). Chem Heterocycl Compd 42, 423–439 (2006). https://doi.org/10.1007/s10593-006-0107-1
Received:
Issue Date:
DOI: https://doi.org/10.1007/s10593-006-0107-1