T. Nakahodo et al. / Tetrahedron Letters 49 (2008) 2302–2305
2305
143.98, 144.32, 144.47, 144.83, 145.68, 145.76, 145.87, 145.93, 145.96,
146.01, 146.10, 146.73, 146.74 (2C), 146.79, 146.81, 146.86, 146.96,
147.12, 147.22, 147.42 (2C), 147.64 (2C), 147.66, 147.81 (2C), 148.98,
148.99, 152.90, 154.27, 156.33, 157.82. 77Se NMR (57.2 MHz,
acetone-d6 capillary in CS2) d 580.0 (relative to Me2Se). MALDI–
TOF MS (m/z) 890 (MÀ). UV–vis absorption ksh 450 nm.
References and notes
13. Akasaka, T.; Ando, W.; Kobayashi, K.; Nagase, S. J. Am. Chem. Soc.
1993, 115, 10366.
14. Hirsch, A.; Gro¨sser, T.; Skiebe, A.; Soi, A. Chem. Ber. 1993, 126,
1061.
1. (a) Hirsch, A.; Brettreich, M. Fullerenes; Wiley-VCH: Weinheim,
2005; (b) Fullerenes: Principles and Applications; Langa, F., Nieren-
garten, J.-F., Eds.; RSC: Cambridge, 2007.
2. Sardona, A. K.; Saini, R. K.; Billups, W. E. Chem. Rev. 2003, 103,
1539.
3. (a) Yamago, S.; Iida, K.; Yoshida, J. J. Am. Chem. Soc. 2002, 124,
2874; (b) Yamago, S.; Iida, K.; Yoshida, J. J. Am. Chem. Soc. 2002,
124, 13666.
4. (a) Ogawa, A.; Tanaka, H.; Yokoyama, H.; Obayashi, A.; Yoko-
yama, K.; Sonoda, N. Tetrahedron 1993, 49, 1177; (b) Ogawa, A.;
Obayashi, A.; Ine, H.; Tsuboi, Y.; Sonoda, N.; Hirao, T. J. Org.
Chem. 1998, 63, 881.
5. Liu, S.-G.; Kreher, D.; Hudhomme, P.; Levillain, E.; Cariou, M.;
Delaunay, J.; Gorgues, A.; Vidal-Gancedo, J.; Veciana, J.; Rovira, C.
Tetrahedron Lett. 2001, 42, 3717.
6. Duczek, W.; Tittelbach, F.; Costtsella, B.; Niclas, H.-J. Tetrahedron
1996, 52, 8733.
15. Compound 3: 1H NMR (500 MHz, acetone-d6 capillary in CS2) d
4.36, 4.50 (ABq, each 1H, J = 12 Hz, CH2), 5.62 (s, 1H, CH), 6.58 (m,
3H, ArH), 6.67 (m, 2H, ArH), 6.90 (t, J = 8 Hz, 1H, ArH), 6.94 (t,
J = 8 Hz, 1H, ArH), 7.26 (t, J = 8 Hz, 2H, ArH). 13C NMR
(125 MHz, acetone-d6 capillary in CS2) d 64.52, 72.96, 73.88, 85.49,
126.37, 127.65 (2C), 127.99, 128.46 (2C), 128.82, 128.96, 131.97,
132.61, 133.60, 135.08, 135.68, 135.75, 136.85, 138.71, 139.28, 140.14,
140.29, 140.70, 141.03, 141.33, 141.52, 141.75, 141.85, 141.89 (2C),
141.93, 141.94, 142.04, 142.15, 142.25, 142.42 (2C), 142.46, 142.58,
142.79, 142.89 (2C), 142.91, 143.51, 144.19, 144.33, 144.46 (2C),
144.47, 144.54, 145.18, 145.19, 145.32, 145.39, 145.44, 145.57, 145.60,
145.74, 145.90, 146.01, 146.11, 146.19, 146.22, 146.39 (2C), 146.40,
147.40, 147.49, 148.19, 150.00, 151.13, 151.74, 155.25. 77Se NMR
(57.2 MHz, acetone-d6 capillary in CS2)
d 549.9 (relative to
7. Ohno, M.; Kojima, S.; Shirakawa, Y.; Eguchi, S. Tetrahedron Lett.
1995, 36, 6899.
8. Ishida, H.; Ohno, M.; Eguchi, S. Tetrahedron Lett. 1999, 40, 1543.
9. Takaguchi, Y.; Katayose, Y.; Yanagimoto, Y.; Motoyoshiya, J.;
Aoyama, H.; Wakahara, T.; Maeda, Y.; Akasaka, T. Chem. Lett.
2003, 32, 1124.
Me2Se). MALDI–TOF MS (m/z) 996 (MÀ), UV–vis absorption ksh
450 nm.
16. Crystal data for 3: C75H12OS2Se, FW = 1072.00, black crystals,
0.20 Â 0.20 Â 0.15 mm3, triclinic, P1 (#2), a = 10.0056(6) A, b =
ꢀ
˚
˚
˚
˚
21.4859(18) A, c = 9.9009(7) A, a = 101.741(3)°, b = 102.084(2)°,
c = 82.923(3)°, V = 2030.5(3) A , Z = 2, Dc = 1.753 mg/m3, T =
100 K, 17,691 reflections, 8081 unique reflections, R1 = 0.0633,
3
10. Fujihara, H.; Ueno, Y.; Chiu, J. J.; Furukawa, N. J. Chem. Soc.,
Chem. Commun. 1991, 1052.
wR2 = 0.1911, GOF = 1.055. The maximum and minimum residual
11. Fujihara, H.; Nakahodo, T.; Furukawa, N. Tetrahedron Lett. 1995,
36, 6275.
electron density is equal to 1.51 and À0.98 e AÀ3. CCDC No. 672026
˚
12. Compound 2: 1H NMR (500 MHz, acetone-d6 capillary in CS2) d
3.91, 4.41 (ABq, each 1H, J = 13 Hz, CH2), 6.86, 7.04, and 7.31 (2H,
1H, and 1H, respectively, C6H4). 13C NMR (125 MHz, acetone-d6
capillary in CS2) d 54.92, 66.30, 69.48, 130.05, 130.54, 130.78, 134.20,
134.81, 136.63, 137.07, 137.22, 137.49, 140.97, 141.53 (2C), 141.87,
142.59, 142.87, 142.88, 143.17 (2C), 143.22, 143.26, 143.30, 143.66,
143.37, 143.43, 143.59 (2C), 143.65, 143.78, 143.84 (2C), 143.85,
contains the supplementary crystallographic data for this Letter. The
by contacting The Cambridge Crystallographic Data Centre, 12
Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.
17. Suzuki, T.; Maruyama, Y.; Akasaka, T.; Ando, W.; Kobayashi, K.;
Nagase, S. J. Am. Chem. Soc. 1994, 116, 1359.