K. Y. Amsharov – M. Jansen · C48 Buckybowl and C60 Fullerene Precursors on the Basis of Truxenone
1507
82.66, 83.42, 83.88, 120.39, 120.53, 123.17, 123.83, 123.93, 3H). – MALDI-TOF MS (DCTB/Ag-triflate): m/z = 946.6
124.35, 126.31, 126.39, 126.53, 127.60, 127.70, 127.93, [M+Ag]+.
129.30, 130.23, 130.35, 130.50, 131.94, 132.06, 132.40,
Syn-5,10,15-triol-5,10,15-tris-naphthalen-2-ylmethyl-10,15-
134.77, 135.22, 137.03, 137.13, 137.79, 141.82, 142.48,
142.93, 148.27, 148.49, 148.64 (6 signals were not observed
due to overlapping). – MALDI-TOF MS (DCTB/Ag-triflate):
m/z = 1000.9 [M+Ag]+. – C48H33Br3O3: calcd. C 64.24,
H 3.71; found C 63.18, H 4.92.
dihydro-5H-diindeno[1,2-a;1ꢀ,2ꢀ-c]fluorene (Xa)
(0.38 g, 23 %). Cream solid. Rf = 0.26 (Et2O/hexane,
1 : 1). – 1H NMR (CDCl3, 300 MHz): δ = 2.32 (s, 3H),
2.62 (d, J = 13.4Hz, 3H), 3.41 (d, J = 13.4Hz, 3H), 6.67 –
6.72 (m, 6H), 6.99 – 7.04 (m, 6H), 7.14 – 7.56 (m, 15H),
7.80 – 7.84 (m, 3H), 8.47 (d, J = 7,7 Hz, 3H). – 13C NMR
(CDCl3, 300 MHz): δ = 43.22, 83.05, 123.98, 125.21,
125.52, 125.89, 126.43, 127.24, 127.38, 127.87, 128.34,
128.95, 129.17, 132.08, 132.75, 132.82, 136.52, 137.12,
143.50, 148.19. – MALDI-TOF MS (DCTB/Ag-triflate):
m/z = 917.2 [M+Ag]+. – C60H42O3: calcd. C 88.86, H 5.22;
found C 88.58, H 5.31.
5,10,15-Tris-(4-bromo-benzylidene)-10,15-dihydro-5H-di-
indeno[1,2-a;1ꢀ,2ꢀ-c]fluorene (VIIIc)
Mixture of several E/Z isomers (201 mg, 82 %). Yellow
solid. Rf = 0.49 (CH2Cl2/PE, 1 : 2). – 1H NMR (CDCl3,
300 MHz): δ = 6.6 – 7.7 (m, 24H), 8.3 – 8.6 (m, 3H). –
MALDI-TOF MS (DCTB/Ag-triflate): m/z = 841.0 [M+H]+,
946.9 [M+Ag]+. – C48H27Br3: calcd. C 68.35, H 3.23; found
C 68.81, H 3.43.
Anti-5,10,15-triol-5,10,15-tris-naphthalen-2-ylmethyl-
Syn-5,10,15-triol-3,8,13-tribromo-5,10,15-tribenzyl-10,15-
10,15-dihydro-5H-diindeno[1,2-a;1ꢀ ,2ꢀ-c]fluorene (Xb)
dihydro-5H-diindeno[1,2-a;1ꢀ,2ꢀ-c]fluorene (IXa)
(0.42 g, 26 %). Yellowish solid. Rf = 0.45 (Et2O/hexane,
1 : 1). – 1H NMR (CDCl3, 300 MHz): δ = 2.03 (s, 1H),
2.35 (s, 1H), 2.39 (s, 1H), 2.56 (d, J = 13.7 Hz, 1H), 3.42
(d, J = 13.7 Hz, 1H), 3.43 (d, J = 13.5 Hz, 1H), 3.46 (d,
J = 13.7 Hz, 1H), 3.87 (d, J = 13.0 Hz, 1H), 3.88 (d, J =
13.0 Hz, 1H), 6.80 – 7.68 (m, 30H), 8.74 (d, J = 7.8 Hz,
1H), 8.82 (d, J = 7.8 Hz, 1H), 8.86 (d, J = 7.7 Hz, 1H). –
13C NMR (CDCl3, 300 MHz): δ = 42.54, 43.55, 43.86,
83.12, 83.82, 84.12, 124.01, 124.35, 125.28, 125.51, 125.57,
126.32, 126.40, 126.47, 126.51, 126.56, 127.36, 127.39,
127.42, 127.46, 127.51, 127.57, 128.93, 129.05, 129.07,
129.17, 129.21, 129.26, 132.09, 132.14, 132.79, 132.83,
132.86, 133.59, 133.62, 133.98, 137.33, 137.39, 137.62,
137.87, 142.30, 142.72, 143.57, 148.62, 148.78, 148.97 (14
signals were not observed due to overlapping). – MALDI-
TOF MS (DCTB/Ag-triflate): m/z = 917.2 [M+Ag]+. –
C60H42O3: calcd. C 88.86, H 5.22; found C 87.71, H 5.62.
(33 mg, 12 %). Yellowish solid. Rf = 0.59 (Et2O/PE,
1 : 1). – 1H NMR (CDCl3, 300 MHz): δ = 2.55 (d, J =
13.3 Hz, 3H), 3.18 – 3.27 (m, 6H), 6.60 – 6.67 (m, 6H),
6.72 (d, J = 8.0 Hz, 3H), 7.00 – 7.38 (m, 12H), 8.49 (s,
3H). – 13C NMR (CDCl3, 300 MHz): δ = 43.77, 82.60,
123.08, 124.92, 126.83, 127.70, 128.86, 130.51, 130.60,
135.05, 135.62, 138.48, 143.93, 146.47. – MALDI-TOF MS
(DCTB/Ag-triflate): m/z = 1000.7 [M+Ag]+.
Anti-5,10,15-triol-3,8,13-tribromo-5,10,15-tribenzyl-10,15-
dihydro-5H-diindeno[1,2-a;1ꢀ,2ꢀ-c]fluorene (IXb)
(102 mg, 38 %). Cream solid. Rf = 0.78 (Et2O/PE, 1 : 1). –
1H NMR ([D6]-DMSO, 300 MHz): δ = 2,15 (d, J = 13.8 Hz,
1H), 2.94 (d, J = 13.8 Hz, 1H), 3.22 (d, J = 13.8, 1H),
3.30 (s, 3H), 3.38 – 3.51 (m, 2H), 3.70 (d, J = 13.8 Hz, 1H),
6.37 (s, 1H), 6.43 – 6.48 (m, 4H), 6.64 (d, J = 8.0, 1H),
6.80 – 6.93 (m, 6H), 6.99 (d, J = 8.0, 1H), 7.06 – 7.21 (m,
5H), 7.06 – 7.21 (m, 3H), 8.93 (s, 1H), 9.02 (s, 1H), 9.12 (s,
1H). – 13C NMR ([D6]-DMSO, 300 MHz): δ = 40.5, 41.09,
42.20, 79.20, 80.00, 81.19, 119.14, 119.37, 119.41, 123.83,
123.99, 124.34, 124.48, 124.55, 125.15, 125.52, 125.58,
126.75, 127.03, 127.11, 127.29, 127.70, 128.11, 128.67,
128.75, 132.76, 133.22, 133.45, 133.55, 133.99, 134.44,
137.43, 137.56, 138.15, 143.11, 143.34, 143.43, 146.37,
146.46, 146.48 (2 signals were not observed due to overlap-
ping). – MALDI-TOF MS (DCTB/Ag-triflate): m/z = 1000.8
[M+Ag]+.
5,10,15-Tris-naphthalen-2-ylmethylene-10,15-dihydro-5H-
diindeno[1,2-a;1ꢀ,2ꢀ-c]fluorene (Xc)
Mixture of several E/Z isomers (336 mg, 86 %). Yellow
solid. Rf = 0.73 (CH2Cl2/PE, 1 : 1). – 1H NMR (CDCl3,
300 MHz): δ = 6.5 – 7.8 (m, 33H), 8.4 – 8.7 (m, 3H). –
MALDI-TOF MS (DCTB/Ag-triflate): m/z = 757.3 [M+H]+,
863.2 [M+Ag]+. – C60H36: calcd. C 95.21, H 4.79; found
C 93.72, H 4.64.
Syn-5,10,15-triol-3,8,13-tribromo-5,10,15-tris-naphthal-
en-2-ylmethyl-10,15-dihydro-5H-diindeno[1,2-a;1ꢀ ,2ꢀ-c]
fluorene (XIa)
5,10,15-Tribenzylidene-3,8,13-tribromo-10,15-dihydro-5H-
diindeno[1,2-a;1ꢀ,2ꢀ-c]fluorene (IXc)
Mixture of several E/Z isomers (68 mg, 90 %). Yel-
(82 mg, 26 %). Cream solid. Rf = 0.39 (Et2O/hexane,
low solid. Rf = 0.31 (CH2Cl2/PE, 1 : 2). – 1H NMR 1 : 1). – 1H NMR (CDCl3, 300 MHz): δ = 2.38 (d, J =
(CDCl3, 300 MHz): δ = 6.85 – 7.8 (m, 24H), 8.35 – 8.75 (m, 13.5 Hz, 3H), 3.20 (d, J = 13.5 Hz, 3H), 3.37 (s, 3H), 6.67 (d,
Unauthenticated
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