Arbeit komplett 12.07.2003 komplett Annahmeste - ArchiMeD

10.4 Cyclisierungen 251
1 H-NMR δ [ppm]:
(300 MHz) Aceton-d6
13 C-NMR δ [ppm]:
(75 MHz) Aceton-d6
1.13 und 1.11 (d, 3 J=6.78, 6H, 2xCH3, 2''-H); 3.20 (dd,
2 J=17.33, 3 J=9.42, 1H, CH2, 1-Ha); 3.63 (dd, 2 J=17.33,
3 J=3.01, 1H, CH2, 1-He); 3.76 (s, 3H, CH3, N-CH3); 3.79 (s,
3H, CH3, 1 IV -H); 3.99 (dd, 3 J=3.39, 3 J=9.42, 1H, CH, 2-Ha);
4.85 (se, 3 J=6.03, 1H, CH, 1''-H); 7.14 (ddd, 3 J=6.03,
3 J=7.16, 4 J=1.51, 1H, CH, 7-H); 7.18 (ddd, 3 J=5.28,
3 J=6.03, 4 J=1.51, 1H, CH, 6-H); 7.42 (dd, 3 J=6.41, 4 J=1.13,
1H, CH, 8-H); 7.71 (dd, 3 J=6.78, 4 J=1.51, 1H, CH, 5-H);
7.94 (s, 1H, CH, 4-H)
22.8 (2xCH3, C-2''); 25.5 (CH2, C-1); 30.9 (CH3, N-CH3);
41.1 (CH, C-2); 52.5 (CH3, C-1 lV ); 69.6 (CH, C-1''); 110.5
(Cq, C-3); 111.7 (CH, C-8); 118.5 (Cq, C-4a); 119.4 (CH, C-
5); 122.6 (CH, C-6); 123.4 (CH, C-7); 127.0 (Cq, C-4b);
133.5 (CH, C-4); 140.0 (Cq, C-9a); 141.8 (Cq, C-8a); 168.8
(Cq, C-1'''); 173.9 (Cq, C-1')
EI-MS (70 eV); m/z (%) 327.2 (_, 45.35), 240.1 (100.00), 208.4 (90.26), 181.0
(41.48), 149.3 (20.60), 106.3 (59.68), 77.2 (22.84), 56.5
(18.55), 43.9 (36.19)
Elementaranalyse (%): Ber.: C: 69.71 H: 6.47 N: 4.28
Gef.: C: 70.04 H: 6.04 N: 4.30
UV/VIS [nm]: lgε
CH2Cl2
λmax: 237.6 (5.37), λ1: 362.0 (5.17), λ2: 312.2 (4.74),
λ3: 269.2 (4.92)
IR (KBr), ö [cm -1 ] 3035 (w) 2977 (m) 2933 (m) 2907 (w) 2877 (w)
1688 (s) 1608 (s) 1523 (m) 1466 (m) 1435 (m)
1395 (m) 1375 (m) 1334 (m) 1311 (m) 1277 (s)
1238 (s) 1199 (m) 1185 (s) 1131 (m) 1108 (s)
1051 (s) 1011 (m) 961 (w) 919 (m) 873 (w)
836 (m) 780 (w) 764 (m) 741 (s)
10.4.1.3 2-tert.-Butyl-3-methyl 9-methyl-2, 9-dihydro-1H-2,3-carbazoldicarboxylat
(97)
7
6
8
5
8a
4b 4a
9
N
CH3
9a
4
3
1 2
H H
1''' 1 IV
CO2CH3
H
CO 2C(CH 3) 3
1'
1'' 2''