Substitution von molekularen Klammern an den Naphthalin ...

Experimenteller Teil
(Kieselgel, Elutionsmittel Chloroform/ Cyclohexan 1:1) gereinigt. Man erhält 5.31 g
(19.5 mmol) 73 als gelben Feststoff (Smp. 221°C); die Ausbeute beträgt 70%.
8.0
7.0
2
3
6.0
1
12
5.0
4 5 6
1 H-NMR (500 MHz, CDCl3): δ [ppm] = 2.50 (d, 1 H, 2 J(13i-H, 13a-H)= 8.2 Hz, 13i-
H), 2.61 (d, 1 H, 13a-H), 4.54 (s, 2H, 6-H, 11-H), 6.52 ( s, 2H, 8-H, 9-H), 7.40 (m, 2
4.0
H, 2-H, 3-H), 7.69 (m, 2H, 1-H, 4-H), 7.73 (s, 2H, 5-H, 12-H).
13 C-NMR (126 MHz, CDCl3): δ [ppm] = 47.74 (d, C-6, C-11), 65.59 (t, C-13),
121.76 (d, C-5, C-12), 126.11 (d, C-2, C-3), 127.84 (d, C-1, C-4), 132.05 (s, C-4a,
C-12a), 135.87 (d, C-8, C-9), 143.67 (s, C-5a, C-11a), 157.08 (s, C-6a, C-10a),
184.01 (s, C=O).
IR (KBr): ν ~ (cm -1 ) = 3050 (C-H), 3018 (C-H), 2930 (C-H), 1650 (C=O), 1580 (C=C).
MS (70 eV), m/z (%): 272 (100) [M + ], 244 (23) [M + -CO], 216 (25) [M + - 2 CO], 190
(15), [M + - CO-CH=CH-CO].
MS (70 eV): Molmasse: 272.084 ber. C19H12O2
11
13
O
O
10
7
9
8
3.0
2.0
266