Substitution von molekularen Klammern an den Naphthalin ...

Experimenteller Teil
rac-94: 1 H-NMR (500 MHz, DMSO-d6): δ [ppm] = 2.35 (dt, 2H, 2 J(19i-H, 19a-H) =
8 Hz, 19i-H, 20i-H), 2.45 (dt, 2H, 19a-H, 20a-H), 3.82 (s, 6H, 21-H, 22-H), 4.57 (s,
4H, 6-H, 8-H, 15-H, 17-H), 7.66 (d, 2H, 3 J(4-H, 3-H) = 8.7 Hz, 4-H, 10-H), 7.70 (s,
2H, 5-H, 9-H), 7.75 (d, 2H, 3-H, 11-H), 7.78 (s, 2H, 14-H, 18-H), 8.27 (s, 2 H, (1-H,
13-H)
13 C-NMR (126 MHz, DMSO-d6): δ [ppm] = 46.85 (d, C-15, C-17), 47.04 (d, C-6, C-
8), 60.89 (q, C-21, C-22), 63.89 (t, C-19, C-20), 119.20 (d, C-5, C-9), 120.42 (d, C-
14, C-18), 124.78 (d, C-3, C-11), 127.30 (d, C-4, C-10), 127.74 (s, C-2, C-12),
130.02 (d, C-1, C-13), 130.80 (s, C-4a, C-9a), 133.98 (s, C-13a, C-18a), 138.58 (s,
C-15a, C-16a), 138.98 (s, C-6a, C-7a), 144.84, 144.96 (s, C-7, C-16), 147.73 (s,
C-5a, C-8a), 149.59 (s, C-14a, C-17a), 167.43 (s, C=O).
Synthese von rac-Ditetrabutylammonium-(6α,8α,15α,17α)-6,8,15,17-
tetrahydro-6,17:8,15-dimethanoheptacen-7,16-dimethoxy-2,11-dicarboxylat
und meso-Ditetra-butylammonium-(6α,8α,15α,17α)-6,8,15,17-tetrahydro-
6,17:8,15-dimethano-heptacen-7,16-dimethoxy-2,12-dicarboxylat 95
HO 2C
MeO
OMe
CO 2H
- O2C
MeO
N(n-Bu) 4 +
61 95
Die Synthese erfolgt analog der Synthesevorschrift zur Darstellung der Klammer
93. Die Ausbeute beträgt 97 % (Smp.:>300°C).
2
OMe
292
CO 2 -