222 JOURNAL OF CHEMICAL RESEARCH 2013
(E)-1-Methoxy-4-(prop-1-enyl)benzene (10): Colourless oil; 1H
NMR (400 MHz, CDCl3) δ 7.27 (d, J = 8.4 Hz, 1H), 6.84 (d, J =
8.8 Hz, 1H), 6.37–6.33 (m, 1H), 6.13–6.07 (m, 1H), 3.80(s, 1H), 1.87
(d, J = 8.0 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ 158.6, 130.8,
130.3, 126.9, 123.4, 113.9, 55.3, 18.4; LRMS (EI, 70 eV) m/z (%):
148 (M+, 100); HRMS (EI) for C10H12O (M+): calcd 148.0888, found
148.0885.
We gratefully acknowledge the scientific and technological
plan of Hunan Province (No. 2011FJ4130), scientific and tech-
nological innovative team of Shaoyang University (2012) for
financial support.
Received 27 December 2012; accepted 5 February 2013
Paper 1201700 doi: 10.3184/174751913X13635315066265
Published online: 19 April 2013
(E)-1-Methyl-2-styrylbenzene (12):30,31 White solid, m.p. 119.1–
120.6 °C (lit. 120–121 °C). Colourless oil; 1H NMR (400 MHz,
CDCl3) δ 7.61 (d, J = 7.6 Hz, 1H), 7.54 (d, J = 7.6 Hz, 2H), 7.40–7.28
(m, 3H), 7.29 (d, J = 7.3 Hz, 1H), 7.25–7.19 (m, 4H), 7.02 (d, J =
16.4 Hz, 1H); 2.45 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 137.7,
136.4, 135.8, 130.4, 130.0, 128.7, 127.6, 127.5, 126.6, 126.5, 126.2,
125.4, 19.9; LRMS (EI, 70 eV) m/z (%): 196 (M++2, 15), 194 (M+,
100), 129 (67), 103 (48), 90 (35).
References
1
2
3
4
5
D. Alberico, M.E. Scott and M. Lautens, Chem. Rev., 2007, 107, 174.
J.-P. Corbet and G. Mignani, Chem. Rev., 2006, 106, 2651.
M. Pretze, P. Große-Gehling and C. Mamat, Molecules, 2011, 16, 1129.
L. Yin and J. Liebscher, Chem. Rev., 2007, 107, 133.
N.T.S. Phan, M. VanDer Sluys and C.W. Jones, Adv. Synth. Catal., 2006,
348, 609.
(E)-1-Nitro-4-styrylbenzene (13): Yellow oil; 1H NMR (400 MHz,
CDCl3) δ 8.22 (d, J = 8.8 Hz, 2H), 7.64 (d, J = 8.8 Hz, 2H), 7.55 (d,
J = 7.2 Hz, 2H), 7.42–7.26 (m, 4H), 7.17–7.12 (d, J = 8.5 Hz, 1H); 13
C
6
J. Hassan, M. Sévignon, C. Gozzi, E. Schulz and M. Lemaire, Chem. Rev.,
NMR (100 MHz, CDCl3) δ 146.8, 143.8, 136.2, 133.3, 128.9, 128.8,
127.0, 126.8, 126.3, 124.1; LRMS (EI, 70 eV) m/z (%): 227 (M++2,
11), 225 (M+, 100), 148 (37), 122 (26); HRMS (EI) for C14H11NO2
(M+): calcd 225.0790, found 225.0787.
2002, 102, 1359.
7
8
J.K. Belardi and G.C. Micalisio, Angew. Chem., Int. Ed., 2008, 47, 4005.
Y. Jia, M. Bois-Choussy and J. Zhu, Angew. Chem., Int. Ed., 2008, 47,
4167.
(E)-1-Nitro-4-(prop-1-enyl)benzene (14): Yellow oil; 1H NMR
(400 MHz, CDCl3) δ 8.20–8.13 (m, 2H), 7.43 (d, J = 10.5 Hz, 2H),
6.46–6.43 (m, 2H), 1.94–1.91 (m, 3H); 13C NMR (100 MHz, CDCl3)
δ 146.4, 144.3, 131.2, 129.4, 126.2, 123.9, 18.5; LRMS (EI, 70 eV)
m/z (%):163 (M+, 100); HRMS (EI) for C9H9NO2 (M+): calcd 163.0633,
found 163.0631.
9
J.K. Stille, Angew. Chem., Int. Ed., 1986, 25, 508.
10 G.A. Grasa and S.P. Nolan, Org. Lett., 2001, 3, 119.
11 A.F. Littke and G.C. Fu, Angew. Chem., Int. Ed., 2002, 41, 4176.
12 J.F. Hartwig, Synlett, 2006, 1283.
13 G. Kerric, E. Le Grognec, F. Zammattio, M. Paris and J.-P. Quintard,
J. Organometal. Chem., 2010, 695, 103.
14 E. Floistrup, P. Goede, R. Stromberg and J. Malm, Tetrahedron Lett., 2011,
52, 209.
15 A. Pal, R. Ghosh, N.N. Adarsh and A. Sarkar, Tetrahedron, 2010, 66,
5451.
16 C.E. Domini, G.F. Silbestri, B.B. Fernández and A.B. Chopa, Ultrason.
Sonochem., 2012, 19, 410.
17 J. Murage, J.W. Eddy, J.R. Zimbalist, T.B. McIntyre, Z.R. Wagner and
F.E. Goodson, Macromolecules, 2008, 41, 7330.
Ethene-1,1-diyldibenzene (15): Colourless oil; 1H NMR (400 MHz,
CDCl3) δ 7.41–7.38 (m, 10H), 5.53(s, 2H), 13C NMR (100 MHz,
CDCl3) δ 150.1, 141.6, 128.3, 128.2, 127.7, 114.3; LRMS (EI, 70 eV)
m/z (%): 182 (M++2, 15), 180 (M+, 100), 103 (47), 28 (86); HRMS
(EI) for C14H12 (M+): calcd 180.0939, found 180.0936.
(E)-1,2-Diphenylethene (16)30,31: Colourless oil; 1H NMR (400 MHz,
CDCl3) δ 7.54 (d, J = 7.6 Hz, 4H), 7.38 (t, J = 7.6 Hz, 4H), 7.30–7.26
(t, J = 7.6 Hz, 1H), 7.24–7.22 (d, J = 7.6 Hz, 1H), 7.13 (s, 2H); 13C
NMR (100 MHz, CDCl3) δ 137.4, 128.8, 128.7, 127.6, 126.5; LRMS
(EI, 70 eV) m/z (%): 180 (M+, 100); HRMS (EI) for C14H12 (M+): calcd
180.0939, found 180.0937.
18 T. Arai, Nucl. Med. Biol., 2012, 39, 702.
19 J.-H. Li, Y. Liang and Y.-X. Xie, Tetrahedron, 2005, 61, 7289.
20 H.-P. Zhang, Y.-Z. Dai, X. Zhou and H. Yu, Synlett, 2012, 23, 1221.
21 A.F. Littke and G.C. Fu, Angew Chem., Int. Ed., 1999, 38, 2411.
22 G.A. Grasa and S.P. Nolan, Org. Lett., 2001, 3, 119.
23 W. Su, S. Urgaonkar and J.G. Verkade, Org. Lett., 2004, 6, 1421.
24 J.B. Beadle, S.H. Korzeniowski, D.E. Rosenberg, B.J. Garcia-Slanga and
G.W. Gokel, J. Org. Chem., 1984, 49, 1594.
25 J.-H. Li and W.-J. Liu, Org. Lett., 2004, 6, 2809.
26 Z.-Y. Tang and Q.-S. Hu, J. Am. Chem. Soc., 2004, 126, 3058.
27 J.-H. Li, Y. Liang, D.-P. Wang, W.-J. Liu, Y.-X. Xie and D.-L.Yin, J. Org.
Chem., 2005, 70, 2832.
(1E,3E)-1,4-Diphenylbuta-1,3-diene (17): Colourless oil; 1H NMR
(400 MHz, CDCl3) δ 7.48–7.41 (m, 4H), 7.38–7.32 (m, 4H), 7.28–
7.24 (t, J = 7.6 Hz, 2H), 7.02–6.95 (m, 2H), 6.74–6.54 (m, 2H), 13C
NMR (100 MHz, CDCl3) δ 137.4, 132.8, 129.7, 128.7, 128.3, 127.1;
LRMS (EI, 70 eV) m/z (%): 208 (M++2, 16), 206 (M+, 100), 129 (46),
103 (86); HRMS (EI) for C16H14 (M+): calcd 206.1096, found
206.1093.
28 L. Liu, Y. Zhang and B. Xin, J. Org. Chem., 2006, 71, 3994.
29 G.W. Kabalka, R.M. Pagni, L. Wang, V. Namboodiri and C.M. Hair, Green
Chemistry, 2000, 2, 120.
30 R.K. Arvela and N.E. Leadbeater, J. Org. Chem., 2005, 70, 1786.
31 R. Cellaa and H.A. Stefani, Tetrahedron, 2006, 62, 5656.
Electronic Supplementary Information
1H NMR and 13C NMR spectra of the products have
been deposited in the ESI available through stl.publisher.
ingentaconnect.com/content/stl/jcr/supp-data