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Supplementary data
Supplementary data associated with this article can be
References and notes
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3. (a) Gorgues, A.; Hudhomme, P.; Salle, M. Chem. Rev.
12. Dong, D.; Liu, Y.; Zhao, Y.; Qi, Y.; Wang, Z.; Liu, Q.
Synthesis 2005, 85.
13. Zhao, Y.-L.; Liu, Q.; Zhang, J.-P.; Liu, Z.-Q. J. Org.
Chem. 2005, 70, 6913.
2004, 104, 5151; (b) Roncali, J. J. Mater. Chem. 1997, 7,
2307; (c) Yamashita, Y.; Tomura, M.; Imaeda, K.
Tetrahedron Lett. 2001, 42, 4191.
4. (a) Ferraro, J. R.; Williams, J. M. Introduction to Synthetic
Electrical Conductors; Academic Press: New York, 1987,
p 1; (b) Kagoshima, S.; Nagasawa, H.; Sambongi, T. One
Dimensional Conductors; Springer: Berlin, 1987, p 1; (c)
Saito, G.; Kagoshiwa, S. The Physics and Chemistry of
Organic Superconductors; Springer: London, 1990, p 1.
14. General procedure for 7a: To a solution of compound 6a
(2.00 mmol, 687 mg) and NaOH (4.00 mmol, 160 mg) in
EtOH–H2O (4:1; v/v, 30 mL) was heated at 60–70 ꢁC for
3–4 h. The reaction mixture was poured into cold water
(50 mL), extracted with diethyl ether (3 · 10 mL), and
dried over anhydrous MgSO4. This extract combined was
`
5. (a) Frere, P.; Skabara, P. J. Chem. Soc. Rev. 2005, 34, 69;
then directly added to a solution of Ni(PPh3)2Cl2
(b) Sarhan, A. A. O. Tetrahedron 2005, 61, 3889; (c)
Boulle, C.; Desmars, O.; Gautier, N.; Hudhomme, P.;
Cariou, M.; Gorgues, A. Chem. Coummun. 1998, 2197; (d)
(0.040 mmol, 26.16 mg), PdCl2 (0.040 mmol, 7.08 mg),
CuI (0.10 mmol, 19.00 mg), and triethylamine (3.00 mmol,
0.42 mL) in THF (30 mL). After the reaction solution was
stirred for 15–20 min at room temperature, the solvent was
removed under reduced pressure, and the residue was
purified by silica gel chromatography (diethyl ether–
hexane = 1/1, v/v) to give the pure 7a (234 mg, 52% yield).
Compound 7a: red crystal; mp 192–194 ꢁC; 1H NMR
(CDCl3, 400 MHz) one isomer d: 1.35 (t, J = 8.0 Hz, 6H),
2.29 (s, 6H), 4.31 (q, J = 8.0 Hz, 4H), 6.49 (s, 2H); the other
d: 1.35 (t, J = 8.0 Hz, 6H), 2.28 (s, 6H), 4.28 (q, J = 8.0 Hz,
4H), 6.43 (s, 2H); IR (KBr, cmꢀ1): 3445, 3065, 2982, 2121,
1668, 1473, 1373, 1285, 1235, 1172, 1029, 933, 761; MS (EI)
m/z 451 [(M+1)]+; calcd (found) for C20H18O4S4: C, 53.31
(53.52); H, 4.03 (4.10).
´
´
Liu, S.-G.; Perez, I.; Martın, N.; Echegoyen, L. J. Org.
Chem. 2000, 65, 9092; (e) Guerro, M.; Lorcy, D. Tetra-
hedron Lett. 2005, 46, 5499.
6. (a) Khanous, A.; Gorgues, A.; Texier, F. Tetrahedron Lett.
1990, 31, 7307; (b) Khanous, A.; Gorgues, A.; Jubault, M.
Tetrahedron Lett. 1990, 31, 7311.
7. Awaji, H.; Sugimoto, T.; Yoshida, Z.-I. J. Phys. Org.
Chem. 1988, 1, 47.
8. (a) Nielsen, M. B.; Moonen, N. N. P.; Boudon, C.;
Gisselbrecht, J.-P.; Seiler, P.; Gross, M.; Diederich, F.
Chem. Commun. 2001, 1848; (b) Nielsen, M. B.; Utesch, N.
F.; Moonen, N. N. P.; Boudon, C.; Gisselbrecht, J.-P.;
Concilio, S.; Piotto, S. P.; Seiler, P.; Gunter, P.; Gross, M.;
¨
Diederich, F. Chem. Eur. J. 2002, 8, 3601.
15. Crystal data for 7a: C20H18O4S4, dark red crystal,
˚
M = 450.58, monoclinic, P2(1)/n, a = 10.7902(8) A, b =
˚
˚
9. (a) Nielsen, M. B.; Petersen, J. C.; Thorup, N.; Jessing,
M.; Andersson, A. S.; Jepsen, A. S.; Gisselbrecht, J.-P.;
Boudon, C.; Gross, M. J. Mater. Chem. 2005, 15, 2599;
(b) Qvortrup, K.; Jakobsen, M. T.; Gisselbrecht, J.-P.;
7.4372(10) A, c = 13.6358(14) A, a = 90ꢁ, b = 102.762(2)ꢁ,
3
˚
c = 90ꢁ, V = 1067.2(2) A , Z = 2, T = 293(2), F000 = 468,
R1 = 0.0762, wR2 = 0.2400. The CCDC deposition num-
ber: 246076.