SHORT PAPER
An Efficient Method for the Synthesis of 1,3,5-Triaroylbenzenes
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1H NMR: = 8.45 (s, 3 H), 7.91 (m, 6 H), 7.55 (m, 6 H), 7.44 (m,
15 H).
13C NMR: = 194.5, 138.4, 133.9, 130.8, 129.0, 128.9, 128.8,
128.4, 127.3, 127.2, 127.1.
References
(1) Pigge, C. F.; Ghsedi, F. Tetrahedron Lett. 2000, 41, 6545.
(2) Pigge, C. F.; Ghsedi, F.; Rath, P. N. J. Org. Chem. 2002, 67,
4547.
(3) Matsuda, K.; Nakamura, N.; Inoue, K.; Koga, N.; Iwamura,
H. Bull. Chem. Soc. Jpn. 1996, 69, 1483.
(4) Rose, J. D.; Statham, F. S. J. Chem. Soc. 1950, 69, 69.
(5) Sasaki, T.; Suzuki, Y. Tetrahedron Lett. 1967, 3137.
(6) Jutz, C.; Wagner, R. M.; Kraatz, A.; Loebering, H. G.
Annalen 1975, 874.
(7) Croxail, W. J.; Van Hook, J. O. J. Am. Chem. Soc. 1949, 71,
2442.
(8) House, H. O.; Reif, D. J.; Wasson, R. L. J. Am. Chem. Soc.
1957, 79, 2490.
(9) Gosselck, J.; Schmidt, G.; Beress, L.; Schenk, H.
Tetrahedron Lett. 1968, 331.
(10) Murahashi, S.-I.; Mitsue, Y.; Tsumiyama, T. Bull. Chem.
Soc. Jpn. 1987, 60, 3285.
(11) Balasubramanian, K. K.; Selvaraj, S. Synthesis 1980, 29.
(12) Elghamry, I. Synth. Commun. 2002, 32, 897.
(13) Elnagdi, M. H.; Elghamry, I.; Kandeel, E.; Abdelrahman, A.
H.; Al-Naggar, A. A.; Amir, S.; Riad, M. Gazz. Chim. Ital.
1997, 127, 291.
(14) Kuckländer, U. Enaminones as Synthones, In The Chemistry
of Enamines; Rappoport, Z., Ed.; John Wiley and Sons: New
York, 1994, 323–636.
(15) (a) Michael, P. J.; Parsons, A. S. Tetrahedron 1996, 52,
2199. (b) Michael, P. J.; Gravestock, D. Synlett 1996, 981.
(16) (a) Greenhill, J. V. Chem. Soc. Rev. 1977, 6, 277. (b) Ping,
L.; Greenhill, J. V. Enaminones in Heterocyclic Synthesis,
Advances In Heterocyclic Chemistry, Vol. 67; Academic
Press: New York, 1997, 203–343.
(17) 1,3,5-Tribenzoylbenzene was found as a minor product
when phenyl ethynyl ketone was treated with acetic acid. For
example see: Johnson, A. W. J. Chem. Soc. 1947, 1626.
MS (EI): m/z (%) = 618 (M+), 181, 152.
UV/Vis (CH3Cl): max = 241, 300 nm.
1,3,5-Tri-(p-chlorobenzoyl)benzene (2e)
Colorless crystals (from ethanol): mp 180 °C (lit.11 179 °C).
IR (KBr): 1665 (C=O) cm–1.
1H NMR: = 8.33 (s, 3 H), 7.77 (m, 6 H), 7.5 (m, 6 H).
13C NMR: = 193.4, 140.0, 138.0, 134.5, 133.8, 131.4, 129.1.
MS (EI): m/z (%) = 494 (M+ + 1), 381, 139.
UV/Vis (CH3Cl): max = 241, 269, 339 nm.
1,3,5-Tri-(p-bromobenzoyl)benzene (2f)
Colorless crystals (from acetone); mp 210.5 °C.
IR (KBr): 1661 (C=O) cm–1.
1H NMR: = 8.39 (s, 3 H), 7.72 (m, 6 H), 7.65 (m, 6 H).
13C NMR: = 193.5, 137.9, 134.9, 133.8, 132.0, 131.4, 128.0.
MS (EI): m/z (%) = 627 (M+ + 3), 238, 182, 155.
UV/Vis (CH3Cl): max = 241, 272, 338 nm.
Acknowledgment
The author is deeply indebted to the Alexander von Humboldt foun-
dation for the award of a research fellowship (Long-Term Coopera-
tion Program) during the period from March 2002 to February 2003
at Göttingen University (Germany).
Synthesis 2003, No. 15, 2301–2303 © Thieme Stuttgart · New York