New precursors for preparing organic conducting materials: synthesis of (R)-hydroxymethylbis(ethylenedithio)tetrathiafulvalene, and the ring expansion of a cyclic sulfate ester

Abstract

The chiral hydroxymethyl-substituted derivative of bis(ethylenedithio)tetrathiafulvalene, has been synthesized from D-mannitol via the cyclic sulfate ester of (2R)-3-(2-methoxyethoxymethoxy)propane-1,2-diol. The latter substance slowly decomposes at 45 °C and should be used when freshly prepared. In contrast, the cyclic sulfate ester of (2R)-3-benzoyloxypropane-1,2-diol containing a five-membered ring, undergoes clean rearrangement at room temperature to the cyclic sulfate ester of 2-benzoyloxypropane-1,3-diol, containing a six-membered ring.

References

1. 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, Prentice Hall Inorganic and Organometallic Chemistry Series, New Jersey, 1992.
2. 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. Stopka, D. Jung and M.-H. Whangbo, Inorg. Chem., 1990, 29, 2555.
3. A. F. Hebard, M. J. Rosseinsky, R. C. Haddon, D. W. Murphy, S. H. Glarum, T. T. M. Palstra, A. P. Ramirez and A. R. Kortan, Nature, 1991, 350, 600.
4. J. D. Wallis, A. Karrer and J. D. Dunitz, Helv. Chim. Acta, 1986, 69, 69.
5. T. Ozturk, C. R. Rice and J. D. Wallis, J. Mater. Chem., 1995, 1553.
6. N. Svenstrup, K. M. Rasmussen, T. K. Hansen and J. Becher, Synthesis, 1994, 809.
7. C. Gemmell, G. C. Janairo, J. D. Kilburn, H. Ueck and A. E. Underhill, J. Chem. Soc., Perkin Trans. 1, 1994, 2715.
8. J. S. Zambounis and C. W. Mayer, Tetrahedron Lett., 1991, 32, 2737.
9. R. Oi and K. B. Sharpless, Tetrahedron Lett., 1991, 32, 999.
10. B. B. Lohray, Y. Gao and K. B. Sharpless, Tetrahedron Lett., 1989, 30, 2623.
11. T. Ozturk, D. C. Povey and J. D. Wallis, Tetrahedron, 1994, 50, 11 205.
12. E. Baer, J. Am. Chem. Soc., 1945, 67, 338.
13. J. LeCocq and C. E. Ballou, Biochemistry, 1964, 3, 976.
14. A. A. Duralski, P. J. R. Spooner and A. Watts, Tetrahedron Lett., 1989, 30, 3585; K. Yamuchi, M. Hihara and M. Kinoshita, J. Chem. Soc. Jpn., 1987, 60, 2169.
15. T. Ozturk, M. Pilkington, C. R. Rice, R. Hoelzl, G. A. Horley, D. A. Tranter, J. D. Wallis, M. M. B. Qayyum and P. Kathirgamanathan, J. Electrochem. Soc. in the press.
16. (a) D. Kotkar, V. Joshi and P. K. Ghosh, J. Chem. Soc., Chem. Commun., 1988, 917; (b) D. Delabouglise and F. Garnier, Synth. Metals, 1990, 39, 117; 1991, 41, 367.
17. G. J. Marshallsay, T. K. Hansen, A. J. Moore, M. R. Bryce and J. Becher, Synthesis, 1994, 926.
18. P. Blanchard, K. Boubekur, M. Sallé, G. Duguay, M. Jubault, A. Gorgues, J. D. Martin, E. Canadell, P. Auban-Senzier, D. Jérome and P. Batail, Adv. Mater., 1992, 4, 579; P. Blanchard, M. Sallé, G. Duguay, M. Jubault and A. Gorgues, Tetrahedron Lett., 1992, 33, 2685.
19. G. J. Marshallsay, M. R. Bryce, G. Cooke, T. Jorgenson, J. Becher, C. D. Reynolds and S. Wood, Tetrahedron, 1993, 49, 6849.
20. G. Lowe and S. J. Salamone, J. Chem. Soc., Chem. Commun., 1983, 1392.
21. B. B. Lohray, Synthesis, 1992, 1035.
22. H. Perst, Oxonium Ions in Organic Chemistry, Verlag Chimie, Weinheim, 1971, p. 110.
23. K. B. Gash and G. U. Yuen, J. Org. Chem., 1966, 31, 4234.
24. G. Steimecke, H. J. Sieler, R. Kirmse and E. Hoyer, Phosphorus Sulfur Relat. Elem., 1979, 7, 59; K. S. Varma, A. Bury, N. J. Harris and A. E. Underhill, Synthesis, 1987, 837.
25. H. Libert, Z. Anal. Chem., 1973, 265, 328.