776
T. Suzuki et al. / Tetrahedron Letters 49 (2008) 772–776
7. (a) Nehira, T.; Parish, C. A.; Jockusch, S.; Turro, N. J.; Nakanishi,
Acknowledgments
K.; Berova, N. J. Am. Chem. Soc. 1999, 121, 8681; (b) Nehira, T.;
Tanaka, K.; Takakuwa, T.; Ohshima, C.; Masago, H.; Pescitelli, G.;
Wada, A.; Berova, N. Appl. Spectrosc. 2005, 59, 121.
National Research Institute of Brewing is gratefully
acknowledged for use of the FDCD instrument. This work
was partly supported by the Global COE Program (Project
No. B01: Catalysis as the Basis for Innovation in Materials
Science) from the Ministry of Education, Science and
Technology, Japan.
8. (a) Katoono, R.; Kawai, H.; Fujiwara, K.; Suzuki, T. Chem.
Commun. 2005, 5154; (b) Suzuki, T.; Iwai, T.; Ohta, E.; Kawai, H.;
Fujiwara, K. Tetrahedron Lett. 2007, 48, 3599; (c) Suzuki, T.; Tanaka,
S.; Kawai, H.; Fujiwara, K. Chem. Asian J. 2007, 2, 171.
9. Tanaka, T.; Tasaki, T.; Aoyama, Y. J. Am. Chem. Soc. 2002, 124,
12453.
10. Crystal data are as follows: 4ꢃbenzene6 solvate: MF
Supplementary data
C44H30N2(C6H6)6, FW 1055.41, orthorhombic Pccn (No. 56),
3
˚
˚
a = 11.899 (1), b = 17.125 (2), c = 29.198 (3) A, V = 5949.5 (9) A ,
q(Z = 4) = 1.178 g cmꢀ3
, T = 153 K, R = 9.0%. CCDC 650120.
Crystallographic data (excluding structure factors) for
the structures in this Letter have been deposited with the
Cambridge Crystallographic Data Centre as supplemen-
tary publication numbers CCDC 650120, 650121, and
666230. 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]. Spectral data and synthetic procedures
of the new compounds and X-ray structure of 1c
(Fig. S1). Supplementary data associated with this article
5ꢃchloroform solvate: MF C38H24N2(CHCl3), FW 628.00, mono-
˚
clinic P21/c (No. 14), a = 10.594 (3), b = 15.113 (5), c = 18.437 (6) A,
3
b = 91.729 (8)°, V = 2950 (1) A , q(Z = 4) = 1.414 g cmꢀ3
,
˚
T = 153 K, R = 4.8%. CCDC 650121. 1cꢃethyl acetate solvate: MF
ꢀ
(C60H52N4O2)2(C4H8O2)3, FW 1986.51, triclinic P1 (No. 2),
˚
a = 15.970 (7), b = 18.706 (7), c = 19.090 (6) A, a = 72.440 (16),
3
˚
b = 76.540 (15), c = 90.01 (2)°, V = 5273 (3) A , q(Z = 2) =
1.251 g cmꢀ3, T = 153 K, R = 16.2%. CCDC 666230.
11. Suzuki, T.; Nishida, J.; Tsuji, T. Angew. Chem., Int. Ed. 1997, 36,
1329.
12. By using Bn–N@C@O in place of chiral isocyanates, an achiral
diamide was obtained, which was then hydrogenated to form dispiro
electron donor 1c with a Bn–NH–CO–CH2CH2CH2 group on each of
the acridane nitrogens. X-ray analysis of 1c demonstrates the presence
of (NH–COꢃ ꢃ ꢃHN–CO)-type hydrogen bond, which is formed inter-
molecularly in the centrosymmetric dyads in the crystal (Fig. S1).
Since the similar dyad formation in the diluted solution is highly
unlikely, the hydrogen bond of (NH–COꢃ ꢃ ꢃHN–CO) would be
formed intramolecularly in less-polar solvents.
13. Berova, N.; Nakanishi, K.; Woody, R. W. Circular Dichroism:
Principles and Applications, 2nd ed.; Wiley-VCH: New York, 2000.
14. Hassey, R.; Swain, E. J.; Hammer, N. I.; Venkataraman, D.; Barnes,
M. D. Science 2006, 314, 1437.
References and notes
1. (a) Lustig, S. R.; Everlof, G. J.; Jaycox, G. D. Macromolecules 2001,
34, 2364; (b) Browne, W. R.; de Jong, J. J. D.; Kudernac, T.; Walko,
M.; Lucas, L. N.; Uchida, K.; van Esch, J. H.; Feringa, B. L. Chem.
Eur. J. 2005, 11, 6414 and 6430; (c) Mori, T.; Inoue, Y. J. Phys. Chem.
A 2005, 109, 2728; (d) Wang, Z. Y.; Todd, E. K.; Meng, X. S.; Gao, J.
P. J. Am. Chem. Soc. 2005, 127, 11552.
15. Ohta, E.; Nehira, T.; Kawai, H.; Fujiwara, K.; Suzuki, T. Tetrahedron
Lett. 2008, 49, 777.
16. (a) Mizutani, T.; Sakai, N.; Yagi, S.; Takagishi, T.; Kitagawa, S.;
Ogoshi, H. J. Am. Chem. Soc. 2000, 122, 748; (b) Ohmori, K.;
Kitamura, M.; Suzuki, K. Angew. Chem., Int. Ed. 1999, 38, 1226; (c)
2. Raymo, F. M. Adv. Mater. 2002, 14, 401.
3. Seminario, J. M.; Tour, J. M. Ann. N.Y. Acad. Sci. 1998, 852, 68.
4. (a) Daub, J.; Salbeck, J.; Aurbach, I. Angew. Chem., Int. Ed. Engl.
1988, 27, 29; (b) Zelikovich, L.; Libman, J.; Shanzer, A. Nature 1995,
374, 790; (c) Westermeier, C.; Gallmeier, H.-C.; Komma, M.; Daub,
J. Chem. Commun. 1999, 2427; (d) Beer, G.; Niederalt, C.; Grimme,
S.; Daub, J. Angew. Chem., Int. Ed. 2000, 39, 3252; (e) Nishida, J.;
Suzuki, T.; Ohkita, M.; Tsuji, T. Angew. Chem., Int. Ed. 2001, 40,
3251; (f) Suzuki, T.; Yamamoto, R.; Higuchi, H.; Hirota, E.; Ohkita,
M.; Tsuji, T. J. Chem. Soc., Perkin Trans. 2 2002, 1937; (g) Higuchi,
H.; Ichioka, K.; Kawai, H.; Fujiwara, K.; Ohkita, M.; Tsuji, T.;
Suzuki, T. Tetrahedron Lett. 2004, 45, 3027.
´
Kwit, M.; Rychlewska, U.; Gawronski, J. New J. Chem. 2002, 26,
1714; (d) Saudan, L. A.; Bernardinelli, G.; Kundig, E. P. Synlett
¨
2000, 483; (e) Superchi, S.; Casarini, D.; Laurita, A.; Bavoso, A.;
Rosini, C. Angew. Chem., Int. Ed. 2001, 40, 451; (f) Yasui, Y.;
Suzuki, K.; Matsumoto, T. Synlett 2004, 619; (g) Mazaleyrat, J.-P.;
Wright, K.; Gaucher, A.; Toulemonde, N.; Dutot, L.; Wakselman,
M.; Broxterman, Q. B.; Kaptein, B.; Oancea, S.; Peggion, C.;
Crisma, M.; Formaggio, F.; Toniolo, C. Chem. Eur. J. 2005, 11,
6921; (h) Masu, H.; Mizutani, I.; Kato, T.; Azumaya, I.; Yamag-
uchi, K.; Kishikawa, K.; Kohmoto, S. J. Org. Chem. 2006, 71,
8037.
5. Suzuki, T.; Ohta, E.; Kawai, H.; Fujiwara, K.; Fukushima, T. Synlett
2007, 851.
6. Suzuki, T.; Migita, A.; Higuchi, H.; Fujiwara, K.; Tsuji, T. Tetra-
hedron Lett. 2003, 44, 6837.