Arbeit komplett 12.07.2003 komplett Annahmeste - ArchiMeD

10 Experimenteller, chemisch-präparativer Teil 288
Molekulargewicht: 321.35
Einsatzmengen: 323 mg (1,0 mmol) 79
Iod
350 ml CH2Cl2
Reaktionsbedingungen: photochemisch hν, 1h
Aufarbeitung: säulenchromatographisch (PE / EE = 4 / 1)
Ausbeute: 129,0 mg (401 µmol; 40%)
Schmelzpunkt: 216-217°C (Essigester/Hexan)
1 H-NMR δ [ppm]:
(300 MHz) CDCl3
13 C-NMR δ [ppm]:
(75 MHz) CD2Cl2
1.50 (t, 3 J=7.16, 3H, CH3, 2''-H); 4.25 (s, 3H, CH3, N-CH3);
4.47 (q, 3 J=7.16, 2H, CH2, 1''-H); 7.33-7.41 (m, 2H, 2xCH,
5-H, 6-H); 7.53 (dd, 3 J=5.28, 4 J=0.75, 1H, CH, 10-H); 7.54
(dd, 3 J=3.01, 4 J=0.75, 1H, CH, 1-H); 8.13 (d, 3 J=7.54, 1H,
CH, 7-H); 8.66 (dd, 3 J=6.03, 3 J(H, F)=9.42, 1H, CH, 2-H);
8.93 (s, 1H, CH, 6-H); 9.03 (dd, 3 J(H, F)=12.81, 4 J=2.64,
1H, CH, 4-H)
14.6 (CH3, C-2''); 34.4 (CH3, N-CH3); 61.0 (CH2, C-1'');
109.7 (CH, C-10); 111.9 (CH, d, 2 J(C, F)=23.74, C-4);
114.8 (CH, d, 2 J(C, F)=24.87, C-2); 117.1 (Cq, C-6a); 117.8
(Cq, d, 4 J(C, F)=4.52, C-5); 119.8 (CH, C-7); 120.8 (CH, C-
8); 123.2 (2xCq, C-6b und C-11b); 125.0 (Cq, d, 3 J(C,
F)=9.04, C-1); 125.7 (CH, C-9); 126.3 (CH, C-6); 133.6 (Cq,
d, 3 J(C, F)=10.17, C-4a); 138.5 (Cq, C-11a); 141.5 (Cq, C-
10a); 161.1 (Cq, d, 1 J(C, F)=244.14, C-3); 167.6 (Cq, C-1')
EI-MS (70 eV); m/z (%) 320.7 (_, 100.00), 292.7 (30.04), 275.5 (47.19), 248.0
(29.46)
Elementaranalyse (%): Ber.: C: 74.75 H: 5.02 N: 4.36
Gef.: C: 73.89 H: 4.95 N: 4.30
UV/VIS [nm]: lgε
CH2Cl2
λmax: 288.0 (5.62); λ1: 346.8 (4.97); λ2: 305.2 (5.08);
λ3: 244.2 (5.41)