Arbeit komplett 12.07.2003 komplett Annahmeste - ArchiMeD

10.4 Cyclisierungen 275
13 C-NMR δ [ppm]:
(75 MHz) DMSO-d6
98.0 (Cq, 4 J(C, F)=4.52, C-5); 108.9 (CH, 2 J(C, F)=22.61,
C-4); 111.7 (CH, C-10); 116.3 (Cq, C-1'); 116.4 (CH, 2 J(C,
F)=24.87, C-2); 117.5 (Cq, C-6a); 118.7 (Cq, C-11b); 120.2
(CH, C-7); 120.5 (CH,C-8); 122.4 (Cq, C-6b); 125.8 (CH, C-
9); 125.9 (CH, 3 J(C, F)=11.03, C-1); 129.1 (CH, C-6); 131.4
(Cq, 3 J(C, F)=9.04, C-4a); 137.8 (CH, C-11a); 138.9 (CH,
C-10a); 160.9 (Cq, 1 J(C, F)=246.40, C-3)
EI-MS (70 eV); m/z (%) 259.9 (_, 100.00), 237.9 (19.93), 231.9 (11.27), 148.7
(14.09), 129.5 (14.06), 57.4 (15.41)
Elementaranalyse (%): Ber.: C: 78.45 H: 3.49 N: 10.76
Gef.: C: 74.67 H: 3.74 N: 8.99
UV/VIS [nm]: lgε
CH2Cl2
λmax: 361.8 (4.82); λ1: 344.2 (3.87); λ2: 302.4 (4.14);
λ3: 285.0 (4.66); λ4: 262.6 (4.21); λ5: 238.8 (4.49)
IR (KBr); ö [cm -1 ] 3492 (w) 3292 (s) 3085 (w) 3055 (w) 2218 (s)
1632 (m) 1603 (m) 1578 (m) 1566 (s) 1502 (m)
1468 (s) 1428 (w) 1400 (w) 1385 (w) 1356 (s)
1329 (w) 1284 (m) 1244 (s) 1215 (w) 1187 (m)
1169 (s) 1152 (m) 1135 (w) 1111 (w) 1076 (w)
1054 (w) 942 (m) 920 (w) 897 (m) 862 (m)
840 (w) 821 (m) 806 (m) 771 (m) 738 (s)
718 (m) 698 (w)
10.4.3.12 11H-Benzo[a]carbazol-3,5-dicarbonsäure-5-methylester (114)
9
8
10
Summenformel: C19H13NO4
Molekulargewicht: 319.31
7
6b 6a
N
H
6
1
CO2CH3
5
4a
11
10a 11a 11b
Einsatzmengen: 400 mg (1,2 mmol) 90
Iod
350 ml CH2Cl2
Reaktionsbedingungen: photochemisch hν, 4h
1'' 1'''
2
4
3
1'
CO2H