Arbeit komplett 12.07.2003 komplett Annahmeste - ArchiMeD

10.4 Cyclisierungen 279
UV/VIS [nm]: lgε
CH2Cl2
λmax: 287.4 (5.63); λ1: 345.0 (5.07); λ2: 247.2 (5.43)
IR (KBr); ö [cm -1 ] 3106 (w) 3053 (w) 3032 (w) 2945 (m) 2922 (w)
2890 (w) 2832 (w) 1698 (s) 1620 (m) 1594 (m)
1580 (m) 1556 (m) 1522 (m) 1482 (s) 1447 (s)
1435 (s) 1413 (w) 1378 (s) 1367 (s) 1337 (s)
1301 (m) 1285 (s) 1252 (s) 1217 (s) 1191 (s)
1176 (s) 1160 (s) 1134 (s) 1072 (s) 1051 (m)
1039 (s) 1027 (s) 972 (w) 938 (m) 912 (m)
877 (w) 857 (w) 835 (w) 786 (s) 755 (s)
746 (s) 703 (w) 691 (m)
10.4.3.15 11-Methyl-11H-benzo[a]carbazol-5-carbonsäure-tert.-butylester (117)
9
8
10
Summenformel: C22H21NO2
Molekulargewicht: 331.41
7
6b 6a
N
CH 3
6
1
CO 2C(CH 3) 3
5
4a
11
10a 11a 11b
Einsatzmengen: 334 mg (1,0 mmol) 66
Iod
350 ml CH2Cl2
Reaktionsbedingungen: photochemisch hν, 3h
1'
2
4
1'' 2''
Aufarbeitung: säulenchromatographisch (PE / EE = 3 / 1)
Ausbeute: 75,4 mg (228 µmol; 23%)
Schmelzpunkt: 169-171°C (Essigester / Hexan)
1 H-NMR δ [ppm]:
(300 MHz) CD2Cl2
3
1.74 (s, 9H, 3xCH3, 2''-H); 4.33 (s, 3H, CH3, N-CH3); 7.35
(ddd, 3 J=6.41, 3 J=6.41, 4 J=1.51, 1H, CH, 8-H); 7.53 (ddd,
3 J=8.29, 3 J=6.41, 4 J=1.13, 1H, CH, 9-H); 7.55-7.67 (m, 3H,
3xCH, 2-H, 3-H, 10-H); 8.18 (d, 3 J=7.91, 1H, CH, 7-H);
8.71-8.75 (m, 1H, CH, 4-H); 8.82 (s, 1H, CH, 6-H); 9.13-
9.18 (m, 1H, CH, 1-H)