Y. Yuan, H. Zhu
FULL PAPER
(t, J = 7.1 Hz, 2 H), 7.98 (d, J = 7.3 Hz, 4 H) ppm. 13C NMR
(150 MHz, CDCl3): δ = 129.0, 129.9, 132.9, 134.8, 194.5 ppm. MS
(EI): m/z = 210 [M]+.
1426, 1309, 1266, 1169, 1027, 885, 853, 758, 741 cm–1. 1H NMR
(600 MHz, CDCl3): δ = 2.43 (s, 3 H), 3.88 (s, 3 H), 6.97 (d, J =
8.8 Hz, 2 H), 7.23 (d, J = 8.0 Hz, 2 H), 7.86 (d, J = 8.1 Hz, 2 H),
7.94 (d, J = 8.7 Hz, 2 H) ppm. 13C NMR (150 MHz, CDCl3): δ =
21.9, 55.6, 114.3, 126.2, 129.7, 130.0, 130.8, 132.4, 146.0, 164.9,
193.4, 194.6 ppm. MS (EI): m/z = 254 [M]+.
1-(3-Methoxyphenyl)-2-phenylethane-1,2-dione (2b):[4g] Yellow solid,
m.p. 90–91 °C. IR (KBr): ν = 3073, 3008, 1662, 1593, 1484, 1453,
˜
1337, 1299, 1204, 1175, 932, 833, 778, 721, 689 cm–1. 1H NMR
(600 MHz, CDCl3): δ = 3.88 (s, 3 H), 7.22 (d, J = 7.9 Hz, 1 H),
7.42 (t, J = 7.4 Hz, 1 H), 7.56–7.49 (m, 4 H), 7.67 (t, J = 6.7 Hz,
1 H), 7.98 (d, J = 6.8 Hz, 2 H) ppm. 13C NMR (150 MHz, CDCl3):
δ = 55.5, 112.8, 121.9, 123.2, 129.0, 129.9, 130.1, 133.0, 134.3,
134.9, 160.1, 194.4, 194.5 ppm. MS (EI): m/z = 240 [M]+.
1,2-Di-p-tolylethane-1,2-dione (2j):[3g] Yellow solid, m.p. 103–
104 °C. IR (KBr): ν = 2919, 1663, 1603, 1447, 1329, 1221, 1172,
˜
1
885, 830, 782, 742 cm–1. H NMR (600 MHz, CDCl3): δ = 2.43 (s,
3 H), 7.30 (d, J = 7.9 Hz, 4 H), 7.86 (d, J = 8.0 Hz, 4 H) ppm.
13C NMR (150 MHz, CDCl3): δ = 20.9, 126.7, 129.0, 129.7, 145.0,
193.5 ppm. MS (EI): m/z = 238 [M]+.
1-(4-Methoxyphenyl)-2-phenylethane-1,2-dione (2c):[4b] Yellow solid,
m.p. 61–62 °C. IR (KBr): ν = 2981, 2943, 1674, 1600, 1572, 1509,
˜
1-(3-Fluorophenyl)-2-(4-methoxyphenyl)ethane-1,2-dione (2k): Yel-
1454, 1300, 1218, 106, 1020, 847, 762, 720 cm–1. 1H NMR
(600 MHz, CDCl3): δ = 3.88 (s, 3 H), 6.97 (d, J = 8.8 Hz, 2 H),
7.51 (t, J = 7.7 Hz, 2 H), 7.65 (t, J = 7.4 Hz, 1 H), 7.98–7.94 (m,
4 H) ppm. 13C NMR (150 MHz, CDCl3): δ = 55.6, 114.4, 126.1,
128.9, 129.9, 132.4, 133.2, 134.7, 165.0, 193.2, 194.9 ppm. MS (EI):
m/z = 240 [M]+.
low solid, m.p. 66–67 °C. IR (KBr): ν = 3075, 2929, 2842, 1671,
˜
1600, 1511, 1443, 1312, 1149, 1026, 929, 884, 850, 783, 744 cm–1.
1H NMR (600 MHz, CDCl3): δ = 3.89 (s, 3 H), 6.99 (d, J = 8.9 Hz,
2 H), 7.36–7.33 (m, 1 H), 7.51–7.46 (m, 1 H), 7.69 (d, J = 9.0 Hz,
1 H), 7.73 (d, J = 7.7 Hz, 1 H), 7.94 (d, J = 8.9 Hz, 2 H) ppm. 13C
NMR (150 MHz, CDCl3): δ = 55.7, 114.5, 116.0, 116.2, 121.8,
121.9, 125.8, 125.9, 130.7, 132.5, 135.2, 162.0, 163.7, 165.2, 192.2,
193.3 ppm. MS (EI): m/z = 258 [M]+. HRMS (EI): calcd. for
C15H11FO3 [M]+ 258.0692; found 258.0691. C15H11FO3 (258.07):
calcd. C 69.76, H 4.29; found C 69.77, H 4.31.
1-Phenyl-2-(p-tolyl)ethane-1,2-dione (2d):[7e] Yellow oil. IR (KBr): ν
˜
= 3062, 2924, 1679, 1601, 1450, 1322, 1213, 1120, 935, 880, 831,
784, 747 cm–1. 1H NMR (600 MHz, CDCl3): δ = 2.44 (s, 3 H), 7.31
(d, J = 8.0 Hz, 2 H), 7.51 (t, J = 7.7 Hz, 2 H), 7.65 (t, J = 7.4 Hz,
1 H), 7.87 (d, J = 8.1 Hz, 2 H), 7.97 (d, J = 7.1 Hz, 2 H) ppm. 13C
NMR (150 MHz, CDCl3): δ = 21.9, 129.0, 129.7, 129.9, 130.0,
130.6, 133.1, 134.8, 146.2, 194.3, 194.8 ppm. MS (EI): m/z = 224
[M]+.
1-(3-Fluorophenyl)-2-(p-tolyl)ethane-1,2-dione (2l): Yellow oil. IR
(KBr): ν = 3072, 2925, 1683, 1602, 1484, 1445, 1306, 1238, 1151,
˜
893, 806, 782, 742, 692 cm–1. 1H NMR (600 MHz, CDCl3): δ =
2.44 (s, 3 H), 7.31–7.36 (m, 3 H), 7.46–7.50 (m, 1 H), 7.69 (d, J =
8.8 Hz, 1 H), 7.73 (d, J = 7.7 Hz, 1 H), 7.86 (d, J = 7.7 Hz, 2 H)
ppm. 13C NMR (150 MHz, CDCl3): δ = 22.0, 116.0, 116.2, 121.8,
121.9, 125.9, 126.0, 129.8, 130.1, 130.3, 130.7, 130.8, 135.1, 135.2,
146.5, 162.0, 163.7, 193.2, 193.4 ppm. MS (EI): m/z = 242 [M]+.
HRMS (EI): calcd. for C15H11FO2 [M]+ 242.0743; found 242.0745.
C15H11FO2 (242.07): calcd. C 74.37, H 4.58; found C 74.36, H 4.57.
1-(2-Methoxyphenyl)-2-phenylethane-1,2-dione (2e):[4d] Yellow solid,
m.p. 70–71 °C. IR (KBr): ν = 2942, 1680, 1599, 1487, 1313, 1273,
˜
1
1208, 1018, 878, 756, 722 cm–1. H NMR (600 MHz, CDCl3): δ =
3.56 (s, 3 H), 6.93 (d, J = 8.3 Hz, 1 H), 7.14 (t, J = 7.4 Hz, 1 H),
7.50 (t, J = 7.8 Hz, 2 H), 7.62–7.58 (m, 2 H), 7.92 (d, J = 7.2 Hz,
2 H), 8.03 (dd, J = 1.6, 7.7 Hz, 1 H) ppm. 13C NMR (150 MHz,
CDCl3): δ = 54.6, 111.3, 120.5, 122.8, 127.7, 128.3, 129.5, 131.9,
132.7, 135.5, 159.4, 192.5, 193.6 ppm. MS (EI): m/z = 240 [M]+.
CCDC-844592 (for 3) contains the supplementary crystallo-
graphic data for this paper. These data can be obtained free of
charge from The Cambridge Crystallographic Data Centre via
www.ccdc.cam.ac.uk/data_request/cif.
1-(4-Chlorophenyl)-2-phenylethane-1,2-dione (2f):[4e] Yellow solid,
m.p. 75–76 °C. IR (KBr): ν = 2924, 1688, 1587, 1450, 1322, 1211,
˜
1
1095, 876, 835, 798, 757, 682 cm–1. H NMR (600 MHz, CDCl3):
Supporting Information (see footnote on the first page of this arti-
δ = 7.48–7.53 (m, 4 H), 7.67 (t, J = 7.0 Hz, 1 H), 7.92 (d, J =
8.4 Hz, 2 H), 7.96 (d, J = 7.9 Hz, 2 H) ppm. 13C NMR (150 MHz,
CDCl3): δ = 129.1, 129.4, 129.9, 131.2, 131.4, 132.8, 135.0, 141.6,
193.0, 193.9 ppm. MS (EI): m/z = 244 [M]+.
1
cle): H and 13C NMR spectra of the prepared compounds.
Acknowledgments
1-(3-Fluorophenyl)-2-phenylethane-1,2-dione (2g):[4c] Yellow solid,
This work was supported by the National Natural Science Founda-
tion of China (20702043) and by the Program for New Century
Excellent Talents in Yangzhou University.
m.p. 65–66 °C. IR (KBr): ν = 3065, 293, 1670, 1588, 1482, 1446,
˜
1323, 1241, 1152, 837, 781, 750, 717 cm–1. 1H NMR (600 MHz,
CDCl3): δ = 7.37 (t, J = 8.2 Hz, 1 H), 7.48–7.54 (m, 3 H), 7.66–
7.71 (m, 2 H), 7.74 (d, J = 7.6 Hz, 1 H), 7.97 (d, J = 8.0 Hz, 2 H)
ppm. 13C NMR (150 MHz, CDCl3): δ = 116.0, 116.2, 121.9, 122.1,
125.9, 126.0, 129.1, 130.7, 130.8, 132.7, 135.1, 162.1, 163.7, 193.0,
193.1, 193.7 ppm. MS (EI): m/z = 228 [M]+.
[1] a) S. E. Wolkenberg, D. D. Wisnoski, W. H. Leister, Y. Wang,
Z. Zhao, C. W. Lindsley, Org. Lett. 2004, 6, 1453; b) X. Deng,
N. Mani, Org. Lett. 2006, 8, 269; c) W. D. Shipe, F. Yang, Z.
Zhao, S. E. Wolkenberg, M. B. Nolt, C. W. Lindsley, Heterocy-
cles 2006, 70, 655; d) I. Held, S. J. Xu, H. Zipse, Synthesis 2007,
1185; e) F. Babudri, V. Fiandanese, G. Marchese, A. Punzi,
Tetrahedron Lett. 1995, 36, 7305; f) N. De Kimpe, E. Stanoeva,
M. Boeykens, Synthesis 1994, 427; g) G. R. Boyce, J. S. John-
son, Angew. Chem. Int. Ed. 2010, 49, 8930; h) E. S. Krongauz,
Russ. Chem. Rev. 1977, 46, 59; i) F. Rong, S. Chow, S. Yan, G.
Larson, Z. Hong, J. Wu, Bioorg. Med. Chem. Lett. 2007, 17,
1663; j) A. J. Herrera, M. Rondon, E. J. Suarez, Org. Chem.
2008, 73, 3384.
1-(2-Methoxyphenyl)-2-(p-tolyl)ethane-1,2-dione (2h):[4f] Yellow so-
lid, m.p. 98–100 °C. IR (KBr): ν = 2946, 1668, 1684, 1462, 1273,
˜
1206, 1112, 1018, 881, 831, 754, 611 cm–1. 1H NMR (600 MHz,
CDCl3): δ = 2.43 (s, 3 H), 3.57 (s, 3 H), 6.93 (d, J = 8.4 Hz, 1 H),
7.13 (t, J = 7.3 Hz, 1 H), 7.29 (d, J = 8.0 Hz, 2 H), 7.60–7.57 (m,
1 H), 7.82 (d, J = 8.1 Hz, 2 H), 8.02 (dd, J = 1.7, 7.8 Hz, 1 H)
ppm. 13C NMR (150 MHz, CDCl3): δ = 20.8, 54.7, 111.4, 120.5,
123.0, 128.4, 128.5, 129.4, 129.5, 135.3, 143.8, 159.4, 192.3,
193.7 ppm. MS (EI): m/z = 254 [M]+.
[2] a) M. H. Nantz, D. A. Lee, D. M. Bender, A. H. Roohi, J. Org.
Chem. 1992, 57, 6653; b) E. C. Taylor, J. E. Macor, L. G.
French, J. Org. Chem. 1991, 56, 1807; c) T. E. Barta, M. A.
1-(4-Methoxyphenyl)-2-(p-tolyl)ethane-1,2-dione (2i):[4e] Yellow so-
lid, m.p. 80–82 °C. IR (KBr): ν = 2938, 1670, 1600, 1570, 1510,
˜
332
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Eur. J. Org. Chem. 2012, 329–333