Chemistry of Heterocyclic Compounds 2015, 51(1), 39–43
165.4; 169.1 (2C). Mass spectrum, m/z (Irel, %): 949 [M]+
(5), 91 (100). Found, %: C 92.45; H 1.06; N 3.12.
C73H9ClN2. Calculated, %: C 92.36; H 0.96; N 2.95.
152.2 (2C); 155.0; 157.1; 160.8; 163.0; 165.2. Mass
spectrum, m/z (Irel, %): 840 [M]+ (2), 91 (100). Found, %:
C 94.12; H 0.53; N 3.42. C66H4N2O. Calculated, %:
C 94.29; H 0.48; N 3.33.
1'-Phenyl-3'-(2-pyridyl)pyrazolino[4',5':1,2][60]-
fullerene (2g). Brown powder. IR spectrum, ν, cm–1: 3150
(=C–H s), 1629 (C=N s), 1600, 1462 (C=C s), 1566, 1491
(C=C s, Py), 881 (=C–H oop. bend, Py), 753, 689 (=C–H
The authors are grateful to University of Kashan for
supporting this work by Grant No. 159196/XXI.
1
oop. bend, Ph) H NMR spectrum, δ, ppm (J, Hz): 7.17
(1H, t, J = 7.5, H Ar); 7.27 (2H, d, J = 8.0, H Ar); 7.36
(1H, t, J = 7.5, H Ar); 7.47 (1H, t, J = 7.5, H Ar); 7.76–
7.90 (2H, m, H Ar); 8.38–8.60 (2H, m, H Ar). 13C NMR
spectrum, δ, ppm: 75.1; 85.9; 111.4; 112.3; 113.4; 114.9
(2C); 116.5; 117.1; 119.2; 121.7; 123.6; 125.2 (2C); 127.1
(2C); 129.0 (2C); 130.2; 133.5; 135.4 (2C); 136.2; 137.1;
138.7 (2C); 140.2 (2C); 141.7; 143.1; 145.0; 146.5; 150.9
(2C); 152.2; 153.7 (2C); 155.1; 157.5; 160.0; 162.2; 164.0;
166.9; 168.0 (2C). Mass spectrum, m/z (Irel, %): 915 [M]+
(5), 91 (100). Found, %: C 94.54; H 0.91; N 4.66.
C72H9N3. Calculated, %: C 94.42; H 0.99; N 4.59.
References
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1'-Phenyl-3'-(2-thienyl)pyrazolino[4',5':1,2][60]-
fullerene (2h). Brown powder. IR spectrum, ν, cm–1: 3150
(=C–H s), 1631 (C=N s), 1600, 1489 (C=C s), 1595, 1428
(C=C s, thiophene), 871 (=C–H oop. bend, thiophene),
8. Okumura, M.; Mikawa, M.; Yokawa, T.; Kanazawa, Y.; Kato, H.;
Shinohara, H. Acad. Radiol. 2002, 9, 495.
1
751, 695 (=C–H oop. bend, Ph). H NMR spectrum,
δ, ppm (J, Hz): 7.13–7.20 (2H, m, H Ar); 7.24 (1H, t,
J = 5.0, H Ar); 7.46–7.52 (3H, m, H Ar); 7.94 (1H, d,
J = 8.0, H Ar); 7.98 (1H, d, J = 8.0, H Ar). 13C NMR
spectrum, δ, ppm: 52.2; 78.2; 123.9 (2C); 124.1; 124.5;
125.4 (2C); 125.9; 126.0; 126.2; 126.8; 127.6; 128.3 (2C);
128.7; 129.1 (2C); 129.3 (2C); 130.0; 130.5; 131.2; 132.5;
133.4; 135.6; 136.8; 137.0; 138.2; 139.7; 140.2; 141.5;
142.0; 143.1 (2C); 144.0; 145.2. Mass spectrum, m/z (Irel, %):
920 [M]+ (4), 91 (100). Found, %: C 92.50; H 0.92;
N 3.10; S 3.82. C71H8N2S. Calculated, %: C 92.60; H 0.88;
N 3.04; S 3.48.
9. Xing, G. M.; Yuan, H.; He, R.; Gao, X. Y.; Jing, L.; Zhao, F.;
Chai, Z. F.; Zhao, Y. L. J. Phys. Chem B. 2008, 112, 6288.
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Chen, Z.; Yuan, H. ; Wang, X.; Long, J.; Chen, C.; Liang, X.;
Zhang, N.; Chai, Z.; Zhao, Y. ACS Nano 2010, 4, 2773.
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Tetrahedron 1998, 54, 2049.
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Soc. 2002, 124, 178.
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Boltalina, O. V. Chem. Heterocycl. Compd. 2004, 40, 1150.
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Ed. 2002, 51, 367.
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Zhu, S. Tetrahedron 2010, 66, 5467.
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Ovchinnikova, N. S.; Goryunkov, A. A.; Kharybin, O. N.;
Nikolaev, E. N.; Yurovskaya, M. A.; Sidorov, L. N.
Tetrahedron 2010, 66, 3037.
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Martin, N. Tetrahedron 2003, 59, 6569.
3'-(2-Furyl)-1'-phenylpyrazolino[4',5':1,2][60]-
–
1
fullerene (2i). Brown powder. IR spectrum, ν, cm : 3100
(=C–H s), 1628 (C=N s), 1600, 1420 (C=C s), 1454, 1400
(C=C s, Fur), 850 (=C–H oop. bend, Fur), 751, 693 (=C–
1
H oop. bend, Ph). H NMR spectrum, δ, ppm (J, Hz):
7.30–7.70 (6H, m, H Ar); 8.90 (2H, d, J = 8.0, H Ar).
13C NMR spectrum, δ, ppm: 76.1; 84.5; 109.6; 111.5;
112.9; 113.1 (2C); 115.6; 116.5; 120.1; 121.3; 123.4; 124.2
(2C); 125.1 (2C); 127.6 (2C); 131.9; 133.2; 134.5 (2C);
135.2; 137.1; 139.6 (2C); 140.1 (2C); 141.0; 143.5; 144.0;
146.1; 151.2 (2C); 152.9; 153.3 (2C); 156.2; 157.5; 159.1;
161.4; 163.6; 165.0; 167.1. Mass spectrum, m/z (Irel, %):
904 [M]+ (10), 91 (100). Found, %: C 94.32; H 0.97;
N 3.19. C71H8N2O. Calculated, %: C 94.24; H 0.89; N 3.10.
3'-(2-Pyridyl)isoxazolo[4',5':1,2][60]fullerene (4e).
–
1
Brown powder. IR spectrum, ν, cm : 3001 (=C–H s),
1630 (C=N s), 1600, 1461 (C=C s, Py), 799 (=C–H
oop. bend, Py). 1H NMR spectrum, δ, ppm (J, Hz): 7.40
(1H, t, J = 8.0, H Py); 7.93 (1H, t, J = 8.0, H Py); 8.47 (1H,
d, J = 7.5, H Py); 8.62 (1H, d, J = 7.5, H Py). 13C NMR
spectrum, δ, ppm: 77.5; 86.1; 110.2; 111.5; 113.4; 115.9
(2C); 116.7; 117.2; 119.8; 122.0; 124.3; 125.1 (2C); 128.9
(2C); 129.5; 130.1; 132.7; 135.6; 136.3; 137.8; 138.4;
139.2 (2C); 141.9; 142.3; 144.5; 146.7; 150.2; 151.8;
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