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J. Harren et al. / Tetrahedron: Asymmetry 9 (1998) 1369–1375
166.28 (2CO), 166.42 (2CO); MS (positive-FAB, m-NBA): m/z=1303.4 (M+[C66H70N4O16S4]+H),
1147.4 (1303.4-Ts), DC (SiO2): Rf=0.29 (trichloromethane:acetone=50:1); C66H70N4O16S4: (1303.54);
CHN analysis calcd (found) C: 60.81 (60.55), H: 5.41 (5.35), N: 4.19 (3.71). Enantiomer separation
by HPLC. Column: cellulose–tris(3,5-dimethylphenylcarbamate) (CDMPC), 250×10 mm. Eluent: n-
hexane:2-propanol=70:30, 2.0 ml min−1. Injection of 25 µl portions of a 4×10−3 molar solution
of 3a in dichloromethane. Pressure: 47 bar. Temperature: 20°C. Detection: UV, λ=254 nm; t0=7.33
min; tr[(+)D]=21.75 min; tr[(−)D]=40.50 min; k0[(+)D]=1.97 min; k0[(−)D]=4.53 min; α=2.30; R=0.28;
[α]25078=412 (c=1.5×10−3; l=10; CH2Cl2) polarimeter Perkin–Elmer 341. CD-measurement: JASCO-
spectropolarimeter J 700, 1.3×10−4 mol/l solution in acetonitrile, 1 mm cell.
4.1.2. 5,7,23,25-Tetrakis(ethoxycarbonyl)-2,11,20,29-tetrakis(4-tolylsulfonyl)-2,11,20,29-
tetraaza[3.3](1,3)(1,2)[3.3](3,4)(1,3)cyclophane 3b
1H NMR (250 MHz, CDCl3): δ=1.20–1.5 (m, 12H, CH2CH3), 2.41 (s, 12H, Ts–CH3), 4.05–4.51 (m,
8H, CH2CH3), 3.40–5.00 (group of broad signals, 16H, ArCH2N), 4.82 (br s, 2H, Har), 7.29–7.90 (m,
20H, Har); MS (positive-FAB, m-NBA): m/z=1303.4 (M+[C66H70N4O16S4]+H), 1147.4 (1303.4-Ts), DC
(SiO2): Rf=0.21 (trichloromethane:acetone=50:1); C66H70N4O16S4 (1303.54).
Acknowledgements
This work was supported by the Deutsche Forschungsgemeinschaft (Sonderforschungsbereich 334:
‘Wechselwirkungen in Molekülen’). The authors wish to thank Dr. S. Grimme (Dept. of Theoretical
Chemistry, Univ. Bonn) for calculation and support concerning theoretical CD.
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