Two isomeric triple-layered tetrathiafulvalenophanes: Syntheses, structures, and electrochemical properties

Tetrahedron Letters

Volumn 38, Issue 17, 1997, Pages 3017-3020

  Yunoki, Shin Ichi ^a   Takimiya, Kazuo ^a   Aso, Yoshio ^a   Otsubo, Tetsuo ^a  

^a HIROSHIMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

TETRATHIAFULVALENE DERIVATIVE;

ARTICLE; CYCLIC POTENTIOMETRY; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTROCHEMISTRY; IN VITRO STUDY; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0030963591     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00523-6     Document Type: Article

References (14)

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2. Takimiya, K.; Aso, Y.; Otsubo, T. Synth. Metals in press.
3. Matsuo, K.; Takimiya, K.; Aso, Y.; Otsubo, T.; Ogura, F. Chem. Lett. 1995, 523.
4. Takimiya, K; Shibata, Y.; Imamura, K.; Kashihara, A.; Aso, Y.; Otsubo, T.; Ogura, F. Tetrahedron Lett. 1995, 36, 5045.
5. Tanabe, J.; Kudo, T.; Okamoto, M.; Kawada, Y.; Ono, G.; Izuoka, A.; Sugawara, T. Chem. Lett. 1995, 579.
6. Otsubo, T.; Aso, Y.; Takimiya, K. Adv. Mater. 1996, 8, 203, and references cited therein.
7. Blanchard, P.; Svenstrup, N.; Becher, J. J. Chem. Soc., Chem. Commun. 1996, 615.
8. Sudmale, I. V.; Tormos, G. V.; Khodorkovsky, V. Y.; Edzina, A. S.; Neilands, O. J.; Cava, M. P. J. Org. Chem. 1993, 58, 1355.
9. All new compounds were characterized by elemental analyses, NMR, and MS spectroscopy.
10. Simonsen, K. B; Svenstrup, N.; Lau, J; Simonsen, O.; Mørk, P.; Kristensen, G. J.; Becher, J. Synthesis 1996, 407.
11. Svenstrup, N.; Rasmussen, K. M.; Hansen, T. K.; Becher, J. Synthesis 1994, 809.
12. 2,3,6,7-Tetrakis(2-methoxycarbonylethylthio)tetrathiafulvalene 19 was prepared by reaction of the zincate 15 and methyl 3-bromopropionate followed by oxidation with mercury (II) diacetate and finally self-coupling reaction of the resulting 4,5-bis(2-methoxycarbonylethylthio)-1,3-dithiole-2-one promoted by methyl phosphite. Use of the same protecting group for tetrathiafulvalenethiolate was described in the 13th Symposium on Fundamental Organic Chemistry (November 1996, Nagoya): Tanabe, J.; Izuoka, A.; Sugawara, T., Saito, T.; Y. Kawada. Abstr. p. 318 (3P61).
13. 26 (including three carbon disulfides per one molecule as a crystal solvent): C, 31.50; H, 2.24 %. Found: C, 31.38; H, 2.35 %.
14. -3, graphite-monochromated Cu-Kα (1.5418 Å) radiation, crystal dimensions 0.62 x 0.23 x 0.20 mm, 2847 unique reflections, R = 0.069 (Rw 0.070).