2-(1,3-benzodithiol-2-ylidene)-1,3-benzoxathiole (dibenzo-oxatrithiafulvalene, DBOTTF): The first tetraheterofulvalene containing oxygen

Tetrahedron Letters

Volumn 37, Issue 17, 1996, Pages 2931-2934

  D'Arcangelis, Samuel T ^a   Cowan, Dwaine O ^a  

^a JOHNS HOPKINS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BENZOXATHIOL DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ELECTROCHEMISTRY;

EID: 0029880205     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00450-9     Document Type: Article

References (21)

1. Ferraris, J.; Cowan, D. O.; Walatka, V.; Perstein, J. H. J. Am. Chem. Soc. 1973, 95, 948 and Coleman, L. B.; Cohen, M. J.; Sandman, D. J.; Yamagishi, F. G.; Garito, A. F.; Heeger, A. J.;Solid State Commun. 1973, 12, 1125.
2. Ferraris, J.; Cowan, D. O.; Walatka, V.; Perstein, J. H. J. Am. Chem. Soc. 1973, 95, 948 and Coleman, L. B.; Cohen, M. J.; Sandman, D. J.; Yamagishi, F. G.; Garito, A. F.; Heeger, A. J.;Solid State Commun. 1973, 12, 1125.
3. For reviews on the history and theory of organic conductors and superconductors, see: Cowan, D. O.; Wiygul, F. M. Chem. Eng. News 7/21 1986, 64, 28-45, Adrian, F. J; Cowan, D. O. Chem. Eng. News 12/21 1992, 70, 24-41, and Bryce, M. R.; Murphy, L. C. Nature 1984, 509, 119-126.
4. For reviews on the history and theory of organic conductors and superconductors, see: Cowan, D. O.; Wiygul, F. M. Chem. Eng. News 7/21 1986, 64, 28-45, Adrian, F. J; Cowan, D. O. Chem. Eng. News 12/21 1992, 70, 24-41, and Bryce, M. R.; Murphy, L. C. Nature 1984, 509, 119-126.
5. For reviews on the history and theory of organic conductors and superconductors, see: Cowan, D. O.; Wiygul, F. M. Chem. Eng. News 7/21 1986, 64, 28-45, Adrian, F. J; Cowan, D. O. Chem. Eng. News 12/21 1992, 70, 24-41, and Bryce, M. R.; Murphy, L. C. Nature 1984, 509, 119-126.
6. Bechgaard, K.; Carneiro, K.; Rasmussen, F. B.; Olsen, M.; Rindorf, G. T.; Jacobsen, C. S.; LaPlaca, S. J.; Pedersen, H. J.; Scott, H. J. J. Am. Chem. Soc. 1981, 103, 2440.
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8. Cowan, D. O., In New Aspects of Organic Chemistry I. Proceedings of the 4th International Kyoto Conference on New Aspects of Organic Chemistry, Yoshida, Z.; Shiba, T.; Ohshiro, Y., Eds., VCH Publishers, New York, 1989, 191.
9. Many reported tetratellurafulvalene complexes are good metals with respect to other C-T complexes and remain metals throughout large temperature domains. No superconducting complexes of tetratellurafulvalene currently exist Only one complex of a tetraselenafulvalene derivative has produced an ambient pressure superconductor. Many ambient pressure superconductors incorporating one of a few derivatives of tetrathiafulvalene (most notably, BEDT-TTF) have been discovered.
10. Bardeen, J.; Cooper, L. N.; Schrieffer, J. R. Phys. Rev. 1957, 708, 1175.
11. According to Ishida, T.; Ishihara, Y.; Yamaga, T.; Nogami, T. Synth. Met. 1993, 56, 1968-1971 and Suzuki, T.; Yamochi, H.; Srdanov, K.; Hinkelmann, K.; Wudl. F. J. Am. Chem. Soc. 1989, 111, 3108-3109, reactions conditions described in Safiev, O. G.; Nazarov, D. V.; Zorin, V. L.; Rakhmankulov, D. L. Khim. Geterotsikl. Soedin. 1988, 6, 852. for the synthesis of Bis-(1,3-benzodioxole)-2-2′-ylidene, (Dibenzotetraoxafulvalene, DBTOF) are not reproducible.
12. According to Ishida, T.; Ishihara, Y.; Yamaga, T.; Nogami, T. Synth. Met. 1993, 56, 1968-1971 and Suzuki, T.; Yamochi, H.; Srdanov, K.; Hinkelmann, K.; Wudl. F. J. Am. Chem. Soc. 1989, 111, 3108-3109, reactions conditions described in Safiev, O. G.; Nazarov, D. V.; Zorin, V. L.; Rakhmankulov, D. L. Khim. Geterotsikl. Soedin. 1988, 6, 852. for the synthesis of Bis-(1,3-benzodioxole)-2-2′-ylidene, (Dibenzotetraoxafulvalene, DBTOF) are not reproducible.
13. According to Ishida, T.; Ishihara, Y.; Yamaga, T.; Nogami, T. Synth. Met. 1993, 56, 1968-1971 and Suzuki, T.; Yamochi, H.; Srdanov, K.; Hinkelmann, K.; Wudl. F. J. Am. Chem. Soc. 1989, 111, 3108-3109, reactions conditions described in Safiev, O. G.; Nazarov, D. V.; Zorin, V. L.; Rakhmankulov, D. L. Khim. Geterotsikl. Soedin. 1988, 6, 852. for the synthesis of Bis-(1,3-benzodioxole)-2-2′-ylidene, (Dibenzotetraoxafulvalene, DBTOF) are not reproducible.
14. Synthesis for a tetrathiafulvalene with oxygens exocyclic with respect to the fulvalene moiety is described in: Suzuki, T.; Yamochi, H.; Srdanov, K.; Hinkelmann, K.; Wudl. F. J. Am. Chem. Soc. 1989, 111, 3108-3109.
15. Bordwell, F. G.; Wolfinger, M. D.; O'Dwyer, J. B. J. Org. Chem. 1974, 39, 2516-2519.
16. Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1345-1353.
17. Bis(dimethylaluminum)-1,2-benzenedithiol was employed in sub-equivalent amounts, because equivalent amounts allowed overreaction, producing some dibenzotetrathiafulvalene (DBTTF), which was very difficult to separate chromatographically from DBOTTF.
18. Mori, T.; Inokuchi, H. Chem. Lett. 1992, 1873-1876.
19. 3).
20. Data obtained from: Lerstrup, K.; Talham, D.; Bloch, A.; Poehler, T.; Cowan, D. O. Chem. Commun. 1982, 336-337.
21. Saito, G.; Ferraris, J. P. Bull. Chem. Soc. Jpn. 1980, 53, 2141-2145.