Arbeit komplett 12.07.2003 komplett Annahmeste - ArchiMeD

10.3 Cyclisierungsedukte 231
Reaktionsbedingungen: Variante A, Heck-Reaktion; 2-3 h erhitzen unter Rückfluß
Aufarbeitung: säulenchromatographisch (PE / EE = 4 / 1)
Ausbeute: 0,17 g (0,6 mmol; 6%)
Schmelzpunkt: 169-170°C (Essigester/Hexan)
1 H-NMR δ [ppm]:
(300 MHz) Aceton-d6
13 C-NMR δ [ppm]:
(75 MHz) Aceton-d6
3.69 (s, 3H, CH3, N-CH3); 5.98 (d, 3 J=16.58, 1H, CH, 2''-H
((E)-Isomer)); 7.26 (d, 3 J=16.58, 1H, CH, 3''-H ((E)-Isomer));
7.30-7.40 (m, 2H, 2xCH, 5-H, 6-H); 7.41 (dd,
3 J=8.85, 3 J=9.04, 2H, 2xCH, 3'-H, 5'-H); 7.58 (d, 3 J=7.16,
1H, CH, 7-H); 7.61 (dd, 3 J=5.46, 4 J(H, F)=5.65, 2H, 2xCH,
2'-H, 6'-H); 7.99 (d, 3 J=7.16, 1H, CH, 4-H)
32.4 (CH3, N-CH3); 91.6 (CH, C-2''); 111.8 (Cq, C-3); 112.6
(CH, C-7); 117.7 (2xCH, 2 J(C, F)=22.61, C-3' und C-5');
121.6 (Cq, C-1''); 121.9 (CH, C-4); 123.8 (CH, C-5); 125.1
(CH, C-6); 126.7 (Cq, C-3a); 127.8 (Cq, 4 J(C, F)=3.39, C-1');
135.1 (2xCH, 3 J(C, F)=7.91, C-2' und C-6'); 139.9 (Cq, C-
7a); 145.1 (CH, C-3''); 146.1 (Cq, C-2); 165.3 (Cq, 1 J(C,
F)=247.53, C-4')
EI-MS (70 eV); m/z (%) 276.1 (_, 100.00), 274.8 (39.49), 260.3 (39.68), 107.0
(11.02)
Elementaranalyse (%): Ber.: C: 78.24 H: 4.74 N: 10.14
Gef.: C: 78.26 H: 4.81 N: 10.15
UV/VIS [nm]: lgε
CH2Cl2
λmax: 339.0 (5.51); λ1: 279.8 (5.46); λ2: 234.6 (5.51)
IR (KBr); ö [cm -1 ] 3462 (w) 3071 (w) 3054 (w) 3024 (w) 2204 (s)
1611 (s) 1575 (m) 1530 (m) 1486 (m) 1470 (s)
1440 (m) 1420 (m) 1404 (m) 1373 (m) 1356 (m)
1341 (w) 1308 (m) 1274 (m) 1253 (m) 1224 (s)
1164 (s) 1137 (m) 1102 (w) 1073 (m) 1035 (w)
1015 (w) 981 (w) 969 (m) 955 (m) 862 (s)
848 (m) 829 (w) 822 (w) 802 (m) 747 (s)
720 (w) 692 (w)