9626
C. Stroh et al. / Tetrahedron Letters 45 (2004) 9623–9626
3. Stroh, C.; Romero, F. M.; Kyritsakas, N.; Catala, L.;
(m, 4H), 7.45 (t, J = 7.5Hz, 1H), 4.54 (s, 1H), 1.09 (s, 6H),
1.05 (s, 6H). 13C (DMSO-d6): 150.8, 143.7, 132.3, 131.5,
131.1, 130.8, 129.1, 126.2, 121.4, 94.8, 90.5, 87.1, 67.1,
25.3, 18.1. IR (KBr pellets): 3179 (mOH), 2927, 2214
(mC„C), 1596, 1540, 1458, 1373, 1262, 1138, 903, 848, 819,
696, 668, 542. Anal. Calcd for C20H23N3O2 (Mr = 337.42):
C, 71.19; H, 6.87; N, 12.45. Found: C, 71.24; H, 6.76; N,
12.08.
Turek, P.; Ziessel, R. J. Mater. Chem. 1999, 9, 875; Miller,
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1995, 7, 221; Cirujeda, J.; Ochande, L. E.; Amigo, J. M.;
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Nakasawa, Y.; Shiomi, D.; Nozawa, K.; Hosokoshi, Y.;
Ishikawa, M.; Takahashi, M.; Kinoshita, M. Chem. Phys.
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13. Rf (SiO2, CH2Cl2/MeCN 4/6): 0.45. MALDI-TOF (1,8,9-
anthracenetriol): 335.9 (65) [M+H]+, 319.9 (100)
[MÀO+H]+, 303.9 (30) [MÀ2O+H]+. IR (KBr pellets):
3449, 3040, 3023, 2975, 2210 (mC„C), 1590, 1449, 1416,
1403, 1393, 1364 (mNO), 1217, 1166, 1138, 1123, 990, 899,
863, 824, 802, 683, 541, 455. UV–vis (CH2Cl2) k nm (e,
4. Stroh, C.; Turek, P.; Rabu, P.; Ziessel, R. Inorg. Chem.
2001, 40, 5334; Rey, P.; Luneau, D. In Magnetism: A
Supramolecular Function; Kahn, O., Ed.; Kluwer Aca-
demic: Dordrecht, 1996; p 431; Inoue, K.; Iwamura, H. J.
Am. Chem. Soc. 1994, 116, 3173; Caneschi, A.; Gatteschi,
D.; Sessoli, R.; Rey, P. Acc. Chem. Res. 1989, 22, 392;
Gatteschi, D.; Laugier, J.; Rey, P.; Zanchini, C. Inorg.
Chem. 1987, 26, 938.
M
À1 cmÀ1): 225 (20490), 282 (36390), 300 (25270), 353 (sh,
7560), 368 (10800), 586 (430), 621 (sh, 415), 682 (sh, 180).
Mp: 122–128°C. Anal. Calcd for C20H20N3O2
(Mr = 334.39): C, 71.84; H, 6.03; N, 12.57. Found: C,
72.02; H, 6.07; N, 12.65.
14. Romero, F. M.; Ziessel, R.; De Cian, A.; Fischer, J.;
Turek, P. New J. Chem. 1996, 20, 919.
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Miyamoto, S.; Iimura, K.; Nakatsuji, M.; Miura, Y. J.
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V.; Berezina, T. A.; Shames, A. I.; Weis, A. L.; Likh-
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Teki, Y. Polyhedron 2001, 20, 1163.
6. Stroh, C.; Mayor, M.; von Ha¨nisch, C.; Turek, P. J. Chem.
Soc., Chem. Commun. 2004, 2050; Tretyakov, E. V.;
Fokin, S. V.; Romanenko, G. V.; Ovcharenko, V. I.
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Videva, V.; Turek, P. J. Org. Chem. 2003, 68,
8025; Vasilevsky, S. F.; Tretyakov, E. V.; Usov, O. M.;
Molin, Y. N.; Fokin, S. V.; Shwedenkov, Y. G.; Ikorskii,
V. N.; Romanenko, G. V.; Sagdeev, R. Z.; Ovcharenko,
V. I. Mendeleev Commun. 1998, 216; Tretyakov, E. V.;
Samoilova, R. I.; Ivanov, Y. V.; Plyusnin, V. F.;
Pashchenko, S. V.; Vasilevsky, S. F. Mendeleev Commun.
1999, 92.
7. Chechik, V.; Wellsted, H. J.; Korte, A.; Gilbert, B. C.;
Caldararu, H.; Ionita, P.; Caragheorgheopol, A. Faraday
Discuss. 2004, 125, 279; Matsushita, M. M.; Ozaki, N.;
Sugawara, T.; Nakamura, F.; Hara, M. Chem. Lett. 2002,
6, 596; Finklea, H. O.; Haddox, R. M. Phys. Chem. Chem.
Phys. 2001, 3, 3431.
8. Park, J.; Pasupathy, A. N.; Goldsmith, J. I.; Chang, C.;
Yaish, Y.; Petta, J. R.; Rinkoski, M.; Sethna, J. P.;
Abrun˜a, H. D.; McEuen, P. L.; Ralph, D. C. Nature 2002,
417, 722.
15. Miura, Y.; Issiki, T.; Ushitani, Y.; Teki, Y.; Itoh, K. J.
Mater. Chem. 1996, 6, 1745.
16. Rf (SiO2, CH2Cl2/MeCN 97/3): 0.18. MALDI-TOF (1,8,9-
anthracenetriol): 359.9 (42) [M+H]+, 343.9 (100)
[MÀO+H]+, 327.9 (30) [MÀ2O+H]+. IR (KBr pellets):
3436, 2977, 2226 (mC„N), 1604, 1502, 1451, 1414, 1392,
1364 (mNO), 1311, 1274, 1220, 1164, 1139, 842, 797, 681,
554, 541, 455. UV–vis (CH2Cl2) k nm (e, MÀ1 cmÀ1): 226
(23480), 285 (34920), 298 (38210), 316 (33830), 586 (465).
Mp: 183–185°C. Anal. Calcd for C22H20N3O2
(Mr = 358.41): C, 73.72; H, 5.62; N, 11.72. Found: C,
73.69; H, 5.53; N, 11.33.
17. Crystal data and structure refinement for 1 and 2:
Data were collected at 200K on a STOE diffractometer
with graphite-monochromated MoKa radiation (k =
˚
0.71073A) using hÀ2h scans. The structures were solved
by direct methods and refined by full-matrix least-squares
analysis. 1, M = 334.39, monoclinic, space group P21/c,
˚
c = 11.164(2)A,
with
a = 14.289(3),
b = 12.149(2),
3
˚
b = 111.44(3)°, V = 1804.1(6)A , Z = 4, Dc = 1.231Mg/
m3, l = 0.081mmÀ1. Parameters (226) were refined using
2302 unique observed reflections [I > 1r(I)] to give
R1 = 0.0745 and wR2 = 0.1349 (all data). Compound 2,
M = 358.41, monoclinic, space group P1/c, with
b =
˚
c = 11.547(2)A,
a = 13.647(3),
b = 12.340(3),
3
3
˚
100.98(3)°, V = 1909.1(7)A , Z = 4, Dc = 1.247Mg/m ,
l = 0.082mmÀ1. Parameters (244) were refined using
2760 unique observed reflections [I > 1r(I)] to give R1 =
0.0589 and wR2 = 0.1081 (all data). Crystallographic data
(excluding structure factors) for the structures in this
paper have been deposited with the Cambridge Crystal-
lographic Data Centre as supplementary publication
numbers CCDC 249046 for 1 and CCDC 249047 for 2,
respectively. Copies of the data can be obtained, free of
charge, on application to CCDC, 12 Union Road,
Cambridge CB2 1EZ, UK [fax: +44(0) 1223 336033 or
e-mail: deposit@ccdc.cam.ac.uk.
9. Ullman, E. F.; Osiecki, J. H.; Boocock, D. G. B.;
Darcy, R. J. Am. Chem. Soc. 1972, 94, 7049; Osiecki, J.
H.; Ullman, E. F. J. Am. Chem. Soc. 1968, 90, 1078.
10. Adapted from Austin, W. B.; Bilow, N.; Kelleghan, W. J.;
Lau, K. S. Y. J. Org. Chem. 1981, 46, 2280.
11. Lamchen, M.; Mittag, T. W. J. Chem. Soc. (C) 1966,
2300.
12. Rf (SiO2, CH2Cl2/MeCN 4/6): 0.35. 1H NMR (DMSO-d6):
8.64–8.62 (m, 2H), 7.87 (s, 2H), 7.72 (br s, 1H), 7.59–7.52