S. Gupta et al. / Tetrahedron 69 (2013) 122e128
127
7.82 (d, J¼8.1 Hz, 1H), 7.66e7.71 (m, 3H), 7.49e7.56 (m, 3H),
7.38e7.47 (m, 1H); 13C NMR (75 MHz, CDCl3)
149.9, 147.3, 137.8,
136.0, 133.8, 133.2, 129.4, 129.2, 128.1, 128.0, 127.8, 127.4, 127.0.
13C NMR (75 MHz, CDCl3)
d
195.4, 138.5, 136.4, 133.7, 131.3, 131.1,
d
130.2, 130.1, 129.1, 128.6, 126.7. HRMS (EIþ): [M]þ, found 216.0331.
C13H9ClO requires 216.0342.
4.5.16. 5-Phenylpyrimidine (4c).26 Isolated as colorless oil; 1H NMR
4.5.28. (4-Fluorobiphenyl)-(4-fluorophenyl)-methanone (7). Isolated
as white solid; observed melting point 143e145 ꢀC; 1H NMR
(300 MHz, CDCl3)
NMR (75 MHz, CDCl3)
d C
9.18 (s, 1H), 8.93 (s, 2H), 7.44e7.58 (m, 5H); 13
d
157.4, 154.1, 134.4, 134.1, 129.5, 129.1, 127.0.
(300 MHz, CDCl3)
d
7.75e7.81 (m, 4H), 7.49e7.58 (m, 4H), 7.057.11 (m,
194.8, 167.1, 164.6, 163.7, 161.4, 144.3,
4H); 13C NMR (75 MHz, CDCl3)
d
4.5.17. 3-(3-Methyl-phenyl)-pyridine (4d).24 Isolated as white solid;
1H NMR (300 MHz, CDCl3)
136.1, 136.0, 133.8, 132.7, 132.6, 131.0, 130.6, 130.2, 129.0, 128.9, 126.9,
116.1, 115.8, 115.7, 115.4. HRMS (EIþ): [M]þ, found 294.0859. C19H12F2O
requires 294.0856.
d
8.89 (d, J¼1.5 Hz, 1H), 8.62 (dd, J¼5.1,
1.5, 1H), 7.90e7.91 (m, 1H), 7.83e7.87 (m, 1H), 7.17e7.36 (m, 4H),
2.36 (s, 3H).
Acknowledgements
4.5.18. 3-(4-Flurophenyl)-quinoline (4e).25 Isolated as white solid;
1H NMR (300 MHz, CDCl3)
d
9.16 (d, J¼2.1, 1H), 8.33 (d, J¼2.1, 1H),
8.21 (d, J¼8.4, 1H), 7.71e7.80 (m, 1H), 7.60e7.71 (m, 4H), 7.23e7.28
(m, 2H); 13C NMR (75 MHz, CDCl3)
We thank the DST, New Delhi for financial support (SR/FT/CS-
017/2010). S.G. is grateful to UGC for the award of fellowship. We
also acknowledge to Prof. S.K. Saha, University of North Bengal, for
helping us to edit the manuscript.
d
164.7, 161.4, 149.0 (JCF¼3.3 Hz),
146.5, 134.1, 133.7 (JCF¼7.4 Hz), 133.4, 133.0, 129.9, 129.5, 129.1
(JCF¼8 Hz), 128.7, 128.0 (JCF¼3.9 Hz), 127.2 (JCF¼26.70 Hz), 116.3
(JCF¼21.5 Hz).
Supplementary data
4.5.19. 1,3-Diphenylbenzene (5a).27 Isolated as white solid; 1H NMR
Supplementary data associated with this article can be found in
(300 MHz, CDCl3)
d
7.81 (m, 1H), 7.65 (dd, J¼8.4, 1.5, 4H), 7.55e7.61
(m, 2H), 7.54 (t, 1H), 7.46e7.49 (m, 3H), 7.44 (t, 1H), 7.35e7.40 (m,
2H); 13C NMR (75 MHz, CDCl3)
127.3, 126.2, 126.1.
d 141.8, 141.2, 129.2, 128.8, 127.4,
References and notes
4.5.20. 1,2-Diphenylbenzene(5b).27 Isolated as pale yellow solid; 1H
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126.42.
d
7.39e7.42 (m, 6H), 7.14e7.21 (m, 8H); 13
141.5, 140.6, 130.6, 129.9, 127.8, 127.4,
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4.5.21. 1,4-Diphenylbenzene (5c).27 Isolated as white solid; 1H NMR
(300 MHz, CDCl3)
d
7.66e7.70 (m, 8H), 7.49 (t, J¼7.2 Hz, 4H),
7.27e7.38 (m, 2H); 13C NMR (75 MHz, CDCl3)
d 140.7, 140.1, 128.8,
127.5, 127.3, 127.0.
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4.5.22. 2,4,6-Triphenylphenol (5d).27 Isolated as white solid; 1H
NMR (300 MHz, CDCl3) 7.63e7.66 (m, 8H), 7.42e7.58 (m, 6H),
7.32e7.37 (m, 3H), 5.48 (s, 1H); 13C NMR (75 MHz, CDCl3)
148.9,
140.5, 137.6, 133.8, 129.4, 129.1, 128.9, 128.8, 128.6, 127.8, 126.9,
126.8.
d
d
ꢁ
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4.5.23. 2,4,6-Triphenylaniline (5e).28 Isolated as pale yellow solid;
1H NMR (300 MHz, CDCl3) 7.23e7.7.60 (m, 8H); 13C NMR (75 MHz,
d
CDCl3)
d 140.9, 140.3, 139.7, 131.1, 129.4, 128.9, 128.7, 128.4, 128.3,
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4.5.24. 2,6-Diphenylpyridine (5f).29 Isolated as white solid; 1H NMR
(300 MHz, CDCl3)
d 8.22e8.27 (m, 4H), 7.81 (m, 1H), 7.70 (d, 2H),
7.48e7.59 (m, 6H); 13C NMR (75 MHz, CDCl3)
d 156.9, 139.5, 137.5,
129.0, 128.7, 127.0, 118.6.
8. (a)Bohm, V.P. W.;Gstottmayr, C.W. K.;Weskamp, T.;Herrmann, W. A. J. Organomet.
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4.5.25. Benzophenone (6a).30 Isolated as white solid; 1H NMR
(300 MHz, CDCl3) 7.72e7.68 (m, 4H), 7.51e7.45 (m, 2H), 7.40e7.35
(m, 4H); 13C NMR (75 MHz, CDCl3)
195.7, 136.5, 131.4, 129.0, 127.2.
d
9. (a) Cavallo, L.; Correa, A.; Costabile, C.; Jacobsen, H. J. Organomet. Chem. 2005,
d
€
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2001, 20, 3848e3850.
4.5.26. Bis(4-fluorophenyl)methanone (6b). Isolated as white solid;
observed melting point 107e109 ꢀC; 1H NMR (300 MHz, CDCl3)
d
7.79e7.84 (m, 4H), 7.14e7.20 (m, 4H); 13C NMR (75 MHz, CDCl3)
11. (a) Hadei, N.; Kantchev, E. A. B.; O’Brien, C. J.; Organ, M. G. Org. Lett. 2005, 7,
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d
193.9, 167.1, 163.7, 133.7, 132.8, 132.6, 132.5, 115.7, 115.4; HRMS
(EIþ): [M]þ, found 218.0547. C13H8F2O requires 218.0543.
€
2314e2317; (d) Jackstell, R.; Frisch, A.; Beller, M.; Rottger, D.; Malaun, M.; Bildstei,
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4.5.27. (2-Chlorophenyl)-phenyl-methanone (6c). Isolated as color-
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3854e3860; (b) Metallinos, C.; Barrett, F. B.; Chaytor, J. L.; Heska, M. E. A. Org.
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less oil; 1H NMR (300 MHz, CDCl3)
d
7.83e7.85 (d, J¼7.8 Hz, 2H),
7.60e7.65 (t, J¼7.5 Hz, 1H), 7.46e7.51 (m, 4H), 7.38e7.44 (m, 2H);