Arbeit komplett 12.07.2003 komplett Annahmeste - ArchiMeD

10.4 Cyclisierungen 289
IR (KBr); ö [cm -1 ] 3489 (w) 3111 (w) 3057 (w) 2977 (m) 2928 (m)
2904 (m) 2862 (w) 1768 (w) 1704 (s) 1624 (m)
1595 (m) 1582 (m) 1563 (s) 1526 (m) 1482 (s)
1473 (s) 1453 (s) 1392 (m) 1377 (s) 1336 (s)
1295 (m) 1281 (m) 1257 (s) 1226 (s) 1210 (s)
1170 (m) 1148 (s) 1124 (s) 1065 (m) 1050 (s)
1032 (w) 937 (m) 911 (w) 886 (m) 811 (s)
782 (m) 767 (s) 756 (s) 742 (m) 724 (w)
680 (w)
10.4.3.22 3-Fluoro-11-methyl-11H-benzo[a]carbazol-5-carbonitril (124)
9
8
10
Summenformel: C18H11FN2
Molekulargewicht: 274.29
7
6b 6a
N
CH3
6
11
10a 11a
Einsatzmengen: 276 mg (1,0 mmol) 82
Iod
350 ml CH2Cl2
Reaktionsbedingungen: photochemisch hν, 1h
Aufarbeitung: säulenchromatographisch (PE / EE = 4 / 1)
1
CN
5
4a
11b
Ausbeute: 120 mg (437 µmol; 44%)
Schmelzpunkt: 219-220°C (Essigester/Hexan)
1 H-NMR δ [ppm]:
(300 MHz) CD2Cl2
1'
2
4
3
4.24 (s, 3H, CH3, N-CH3); 7.35-7.56 (m, 4H, 4xCH, 2-H, 8-
H, 9-H, 10-H); 7.96 (dd, 3 J(H, F)=10.17, 4 J=2.63, 1H, CH,
4-H); 8.04 (dd, 3 J=7.91, 4 J=1.13, 1H, CH, 7-H); 8.65 (dd,
3 J=9.42, 4 J(H, F)=5.28, 1H, CH, 1-H)
F