1396
Acknowledgements
Support for this work by the Ministry of Education of the Republic of Korea (BSRI-98-3433) and by
the Center for Biofunctional Molecules is gratefully acknowledged. NMR and mass spectra were taken
at the Center for Research Facilities at the Chungnam National University and the Korea Basic Science
Center, respectively.
References
1. Breitenbach, J.; Boosfeld, J.; Vogtle, F. In Comprehensive Supramolecular Chemistry; Vogtle, F., Ed.; Elsevier Science, 1996;
Vol. 2, pp. 29–67.
2. Vogtle, F. Cyclophane Chemistry; Wiley: Chichester, 1993.
3. Compound 1: mp 175–176°C; 1H NMR (DMSO-d6) δ 5.21 (s, 4H, -OCH2-C6H4-CH2O-), 6.65–6.58 (m, 4H, two Ar-H ortho
to -OH and two Ar-H para to -OH), 7.7–7.4 (m, 16H, Ar-H), 11.95 (broad s, 2H).
4. Compound 2: mp 172°C; 1H NMR (CDCl3) δ 1.0–0.9 (m, 4H, -OCH2CH2(CH2)2CH2CH2O-), 1.35–1.2 (m, 4H, -OCH2CH2-
(CH2)2CH2CH2O-), 3.59 (t, J=6 Hz, 4H, -OCH2(CH2)4CH2O-), 5.27 (s, 4H, -OCH2-C6H4-CH2O-), 6.26 (d, J=2 Hz, 2H, Ar-H
ortho to -O(CH2)6-), 6.71 (dd, J=8 and 2 Hz, 2H, Ar-H para to -O(CH2)6-), 7.5-7.3 (m, 12H, Ar-H), 7.70 (dd, J=7 and 2 Hz,
4H, Ar-H ortho to C_O in two benzoyl groups); 13C NMR (CDCl3) δ 23.6, 27.0, 67.8, 69.8, 99.1, 109.3, 121.7, 126.7, 127.9,
129.3, 131.9, 132.1, 136.8, 139.0, 158.9, 162.0, 195.8; mass (EI) 104 (100), 105 (96), 215 (26), 316 (42), 317 (90), 508 (53),
612 (99, M+), 613 (43); anal. calcd for C40H36O6: C, 78.41; H, 5.92. Found: C, 78.34; H, 5.60.
5. Compound 3: mp 220–223°C; 1H NMR (CDCl3) δ 0.9–0.8 (m, 8H, -OCH2CH2(CH2)2CH2CH2O-), 1.35–1.2 (m, 8H,
-OCH2CH2(CH2)2CH2CH2O-), 3.72 (t, J=6 Hz, 8H, -OCH2(CH2)4CH2O-), 5.14 (s, 8H, -OCH2-C6H4-CH2O-), 6.51 (d, J=2
Hz, 4H, Ar-H ortho to -O(CH2)6-), 6.62 (dd, J=8 and 2 Hz, 4H, Ar-H para to -O(CH2)6-), 7.5–7.3 (m, 24 H, Ar-H), 7.71 (dd,
J=7 and 2 Hz, 8H, Ar-H ortho to C_O in four benzoyl groups); 13C NMR (CDCl3) δ 24.7, 28.3, 67.8, 69.9, 100.3, 111.5,
122.2, 127.8, 127.9, 129.4, 132.0, 132.2, 136.5, 139.3, 159.0, 162.4, 198.0; mass (positive ion FAB) 1225.50 (M++H+); anal.
calcd for C80H72O12: C, 78.41; H, 5.92. Found: C, 78.67; H, 5.95.
6. (a) Lappin, G. R.; Zannucci, J. S. J. Org. Chem. 1971, 36, 1808–1811; (b) Wagner, P. J.; Meador, M. A.; Scaiano, J. C. J.
Am. Chem. Soc. 1984, 106, 7988–7989; (c) Sumathi, T.; Balasubramanian, K. K. Tetrahedron Lett. 1992, 33, 2213–2216;
(d) Abdul-Aziz, M.; Auping, J. V.; Meador, M. A. J. Org. Chem. 1995, 60, 1303–1308; (e) Sharshira, E. M.; Okamura, M.;
Hasegawa, E.; Horaguchi, T. J. Heterocyclic Chem. 1997, 34, 861–869.
7. Ace micro photochemical reactor with quartz well purchased from Aldrich was used.
8. Compound 5: mp 271°C; 1H NMR (CDCl3) δ 1.67 (broad s, 4H, -CH2(CH2)2CH2-), 2.78 (broad s, 4H, -CH2(CH2)2CH2-),
5.28 (s, 4H, -OCH2-C6H4-CH2O-), 6.49 (d, J=2 Hz, 2H, C7-H of benzofuran ring), 6.98 (dd, J=8 and 2 Hz, 2H, C5-H of
benzofuran ring), 7.5–7.3 (m, 16 H, Ar-H); 13C NMR (CDCl3) δ 26.3, 27.2, 69.7, 96.9, 113.4, 117.3, 119.7, 121.8, 126.7,
126.9, 128.7, 129.1, 132.9, 136.9, 153.0, 154.5, 155.5; mass (EI) 104 (21), 165 (13), 444 (19), 576 (100, M+), 577 (44); anal.
calcd for C40H32O4: C, 83.31; H, 5.59. Found: C, 83.47; H, 5.33.
9. Slow evaporation from chloroform solution afforded a colorless crystal suitable for diffraction study. Crystal data for 5:
monoclinic, space group C2/c, a=16.945(3) Å, b=11.339(1) Å, c=16.529(5) Å, β=109.45(2)°, V=2994(1) Å, Z=4. A list of
atomic coordinates and bond distances has been deposited at the Cambridge Crystallographic Data Center.