R. Suleiman, J. Tijani and B. El Ali
SpectralandAnalyticalDataforsomeα,β-unsaturatedAmides
N,N-diisobutyl-2-phenylpropeneamide (3ab1)
has been funded by King Fahd University of Petroleum and
Minerals under project no. CY/Palladium/295.
Oil, IR (CHCl3) v (cm−1) 1633 (CO); 1H NMR δ (CDCl3): 0.71 [d, 6H,
CH(CH3)2, J = 5.0 Hz], 0.91 [d, 6H, CH(CH3)2, J = 5.0 Hz], 1.82 References
[m, 1H, CH(CH3)2], 2.10 [m, 1 H, CH(CH3)2], 2.99 (d, 2 H, NCH2,
[1] R. Skoda-Fo¨ldes, L. Kolla´r, Curr. Org. Chem. 2002, 6, 1097.
J = 7.5 Hz), 3.31 (d, 2 H, NCH2, J = 7.5 Hz), 5.28 (d, 1 H, CH2,
J = 1.5 Hz), 5.64 (d, 1 H, CH2, J = 1.5 Hz), 7.22–7.45 (m, 5 H
arom.); 13C NMR δ (CDCl3): 19.0 (CH3)2, 19.4 (CH3)2, 25.4 (CH), 26.0
(CH), 50.4 (NCH2), 54.9 (NCH2), 113.6 ( CH2), 125.0 (C4ꢁ), 127.6
(C3ꢁ, C5ꢁ), 127.8 (C2ꢁ, C6ꢁ), 135.5 (C1ꢁ), 145.4 (C CH2), 170.4 (C O);
GC-MS m/z 259 (M+); analysis calculated for C17H25NO (259.38): C,
78.72; H, 9.71; N, 5.40. Found: C, 78.69; H, 9.83; N, 5.54.
[2] a) B. Cornils, W. A. Herrmann, (Eds.), Applied Homogeneous Catalysis
with Organometallic Compounds, Wiley-VCH: Weinheim, 1996; b)
M. Beller, C. Bolm, (Eds.), Transition Metals for Organic Synthesis,
Wiley-VCH: Weinheim, 1998, Vols I and II.
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M. Mizugaki, T. Sakamoto, H. Fukuda, Chem. Pharm. ull. 1986, 34,
1643; b) O. Kitagawa, K. Aoki, T. Inoue, T. Taguchi, Tetrahedron Lett.
1995, 36, 593; c) C. Andres, J. P. Duque-Soladana, R. Pedrosa, J. Org.
Chem. 1999, 64, 4282.
[4] M. J. Caulfield, G. G. Qiao, D. H. Solomon, Chem. Rev. 2002, 102,
3067.
N-hexyl-2-phenylpropenamide (3ab2)
[5] C. Bianchini, G. Mantovani, A. Meli, W. Oberhauser, P. Bruggeller,
T. Stampfl, J. Chem. Soc., Dalton Trans. 2001, 690.
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42, 1567.
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41, 5761.
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1993, 6, 409.
1
Oil, IR (CHCl3) v (cm−1) 1657 (CO), 3299 (NH); H NMR δ (CDCl3):
0.83 (t, 3 H, CH3CH2, J = 7.7 Hz), 1.21–1.48 [m, 6 H, -(CH2)3-],
2.31 (m, 2H, NCH2CH2), 3.28 (t, 2 H, NCH2, J = 6.4 Hz), 5.56 (s, 1
H, CH2), 5.98 (s, 1 H, CH2), 6.30 (s, 1 H, NH), 7.11–7.72 (m,
5 H arom.); 13 C NMR δ (CDCl3): 14.0 (CH3), 22.5 (CH3CH2), 26.5
(CH3CH2CH2CH2), 29.3 (CH3CH2CH2CH2), 31.4 (NCH2CH2), 39.9
(NCH2), 120.8 ( CH2), 125.9 (C4ꢁ), 127.9 (C3ꢁ, C5ꢁ), 128.6 (C2ꢁ, C6ꢁ),
137.0 (C1ꢁ), 145.1 (C CH2), 167.8 (C O); GC-MS m/z 231 (M+);
analysis calculated for C15H21NO (231.33): C, 77.88; H, 9.15; N, 6.05.
Found: C, 78.02; H, 9.04; N, 6.17.
N-cyclohexyl-2-phenylpropenamide (3ab3)
1
Oil, IR (CHCl3) v (cm−1) 1641 (CO), 3279 (NH); H NMR δ (CDCl3):
[17] U. Matteoli, A. Scrivanti, V. Beghetto, J. Mol. Catal. 2004, 213, 183.
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151, 47.
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58, 213.
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10, 1519.
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Organonometallic 1992, 11, 1598.
0.83–2.33 [m, 10 H, -(CH2)5-], 3.88 (m, 1 H, NCH), 5.58 (d, 1 H, CH2,
J = 1.6 Hz), 5.79 (s, 1 H, NH), 6.03 (d, 1 H, CH2, J = 1.6 Hz),
6.98–7.48 (m, 5 H arom.); 13C NMR δ (CDCl3): 24.7 (2CH2), 25.7
(CH2), 32.8 (2CH2), 48.5 (NCH), 121.2 ( CH2), 125.9 (C4ꢁ), 127.9
(C3ꢁ, C5ꢁ), 128.6 (C2ꢁ, C6ꢁ), 137.0 (C1ꢁ), 145.1 (C CH2), 166.6 (C O);
GC-MS m/z 229 (M+); analysis calculated for C15H19NO (229.32): C,
78.56; H, 8.35; N, 6.11. Found: C, 78.69; H, 8.41; N, 5.97.
[23] A. K. Paviglianiti, D. J. Minn, W. C. Fultz, J. L. Burmeister, Inorg. Chim.
Acta. 1989, 159, 65.
N-benzyl-2-phenylpropenamide (3ab4)
[24] V. N. Zudin,
V. D. Chinakov,
V. M. Nikipelov,
V. A. Rogov,
V. A. Likholobov, Y. I. Ermakov, J. Mol. Catal. 1989, 52, 27.
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84, 165.
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[28] I. Del Rio, N. Ruiz, C. Claver, L. A. vanVeen, P. W. N. M. van Leeuwen,
J. Mol. Catal. 2000, 161, 39.
[29] A. Vavasori, G. Cavinato, L. Toniolo, J. Mol. Catal. 2001, 176, 11.
[30] Yuichi Kushino, Kenji Itoh, Masahiro Miura, Masakatsu Nomura,
J. Mol. Catal. 1994, 89, 151.
1
Oil, IR (CHCl3) v (cm−1) 1652 (CO), 3403 (NH); H NMR δ (CDCl3):
4.14 (s, 1 H, NH), 4.37 (s, 2 H, NCH2), 5.50 (s, 1 H, CH2), 5.90 (s,
1 H, CH2), 6.79–7.62 (m, 10 H arom.); 13C NMR δ (CDCl3): 43.1
(NCH2), 120.7 (C4ꢁ), 125.4 (C4 benzyl), 126.5 (C3ꢁ, C5ꢁ), 126.8 (C3,
C5 benzyl), 127.4 (C2ꢁ, C6ꢁ), 127.8 (C2, C6 benzyl), 136.2 (C1ꢁ), 137.8
(C1 benzyl), 144.3 (C CH2), 167.6 (C O); GC-MS m/z 237 (M+);
analysis calculated for C16H15NO (237.29): C, 80.98; H, 6.37; N, 5.90.
Found: C, 80.86; H, 6.45; N, 5.98.
[31] Wen Rui-ming, Luo Xin-xiang, Yu Shan-xin, Zhang Lu-xi, Hecheng
Huaxue 2001, 9, 269.
Acknowledgments
We thank King Fahd University of Petroleum and Minerals (KFUPM-
Saudi Arabia) for providing all support to this project. This project
c
Copyright ꢀ 2009 John Wiley & Sons, Ltd.
Appl. Organometal. Chem. 2010, 24, 38–46