The Synthesis of (E)-1,2-Disubstituted Ethenes
J. Chin. Chem. Soc., Vol. 50, No. 4, 2003 895
General procedure for preparation of (E)-1,2-disub-
stituted ethenes (6)
2H), 7.17-7.30 (m, 5H); IR nmax (film) 3027, 2963, 1603,
1494, 1453, 1378, 967, 909, 734 cm-1.
To a suspension of b-hydroxyalkyl selenides resin (1.0
g) swollen in CH2Cl2 (10 mL) and containing triethylamine
(7 mmol) was added thionyl chloride (2 mmol) at room tem-
perature and stirred for 4 h. After the resin was filtered off
and washed with CH2Cl2, the filtrate was washed with brine,
dried over Na2SO4, and evaporated to give the crude product,
which was purified by preparative TLC on silica gel.
(E)-Stilbene (6a)10
(E)-1-Phenyl-1-pentene (6j)13
1
Colorless oil; H-NMR d 0.97 (t, J = 7.3 Hz, 3H),
1.45-1.54 (m, 2H), 2.16-2.22 (m, 2H), 6.19-6.26 (m, 1H),
6.40 (d, J = 15.8 Hz, 1H), 7.16-7.35 (m, 5H); IR nmax (film)
3025, 2958, 1653, 1598, 1449, 1378, 963, 738 cm-1.
(E)-1-Phenyl-2-hexene (6k)15
1
Colorless oil; H-NMR d 0.92 (t, J = 7.4 Hz, 3H),
1.35-1.42 (m, 2H), 1.98-2.03 (m, 2H), 3.34 (d, J = 6.1 Hz,
2H), 5.48-5.59 (m, 2H), 7.16-7.30 (m, 5H); IR nmax (film)
3027, 2959, 1653, 1603, 1494, 1378, 965, 744 cm-1.
mp 121.5-123 °C (lit. 122-123 °C); 1H-NMR d 7.12 (s,
2H), 7.18-7.21 (m, 2H), 7.36-7.43 (m, 4H), 7.48-7.55 (m,
4H); IR nmax (KBr) 3019, 1579, 1468, 1072, 962, 910, 765,
693 cm-1.
(E)-1-Phenyl-2-(p-chlorophenyl)ethene (6b)10
ACKNOWLEDGMENT
1
mp 127-128 °C (lit. 126-127 °C); H-NMR d 7.10 (s,
2H), 7.26-7.48 (m, 9H); IR nmax (KBr) 3025, 1585, 1465, 945,
815, 699 cm-1.
Support by the National Science Foundation of China
(No. 29932020) is gratefully acknowledged.
(E)-1-Phenyl-2-(p-methylphenyl)ethene (6c)10
1
mp 116-117 °C (lit. 116-117 °C); H-NMR d 2.35 (s,
3H), 7.04 (s, 2H), 7.10-7.60 (m, 9H); IR nmax (KBr) 3025,
2977, 1595, 1468, 941, 820, 705 cm-1.
Received September 19, 2002.
(E)-1-Phenyl-2-(m-methylphenyl)ethene (6d)10
mp 46-47 °C (lit. 47-48 °C); 1H-NMR d 2.32 (s, 3H),
7.01 (s, 2H), 7.08-7.65 (m, 9H); IR nmax (KBr) 3029, 2970,
1594, 1466, 950, 818, 705 cm-1.
REFERENCES
1. For recent reviews on SPOS, see: (a) Fruchtel, J. S.; Jung, G.
Angew. Chem., Int. Ed. 1996, 35, 17. (b) Hermkens, P. H. H.;
Ottenhijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643.
(c) Brown, R. C. D. J. Chem. Soc., Perkin Trans. 1 1998,
3293. (d) Lorsbach, B. A.; Kurth, M. J. Chem. Rev. 1999, 99,
1549. (e) Guillier, F.; Orain, D.; Bradley, M. Chem. Rev.
2000, 100, 2091. (f) Sammelson, R. E.; Kurth, M. J. Chem.
Rev. 2001, 101, 137.
(E)-1-Phenyl-1-propylene (6e)11
1
Colorless oil; H-NMR d 1.87 (d, J = 1.5 Hz, 3H),
6.21-6.27 (m, 1H), 6.42 (d, J = 16.9 Hz, 1H), 7.0-7.35 (m,
5H); IR nmax (film) 3028, 2972, 1600, 1495, 1445, 956, 728
cm-1.
(E)-1-Phenyl-1,4-pentadiene (6f)12
Colorless oil; 1H-NMR d 2.95-2.98 (m, 2H), 5.05-5.09
(m, 2H), 5.87-5.92 (m, 1H), 6.21-6.26 (m, 1H), 6.43 (d, J =
15.9 Hz, 1H), 7.20-7.37 (m, 5H); IR nmax (film) 3026, 2978,
1600, 1496, 1449, 965, 913, 742 cm-1.
2. Paulmier, C., Ed.; Selenium Reagents and Intermediates in
Organic Synthesis; Pergamon Press: Oxford, 1986.
3. (a) Sharpless, K. B.; Lauer, R. F. J. Am. Chem. Soc. 1973, 95,
2697. (b) Dumont, W.; Bayet, P.; Krief, A. Angew. Chem.,
Int. Ed. 1974, 13, 804. (c) Seebac, D.; Beck, A. K. Angew.
Chem., Int. Ed. 1974, 13, 805. (d) Dumont, W.; Krief, A.
Angew. Chem., Int. Ed. 1975, 14, 350. (e) Van Ende, D.;
Dumont, W.; Krief, A. Angew. Chem., Int. Ed. 1975, 14, 700.
(f) Van Ende, D.; Krief, A. Tetrahedron Lett. 1975, 16, 457.
(g) Lémion, A. M.; Krief, A. Tetrahedron Lett. 1976, 17,
3227. (h) Sevrin, M.; Dumont, W.; Hevesi, L.; Krief, A. Tet-
rahedron Lett. 1976, 17, 2647.
4. (a) Lerouge, P.; Paulmier, C. Bull. Soc. Chim. Fr. 1985,
1219; Related a-Selenenylating Aldehydes, see: (b) Reich,
H. J.; Renga, J. M. J. Org. Chem. 1975, 40, 3313. (c) Jefson,
M.; Meinwald, J. Tetrahedron Lett. 1981, 22, 3561.
5. (a) Rémion, J.; Dumont, W.; Krief, A. Tetrahedron Lett.
1976, 17, 1385. (b) Rémion, J.; Krief, A. Tetrahedron Lett.
(E)-1-Phenyl-1-butene (6g)13
Colorless oil; 1H-NMR d 1.07 (t, J = 7.2 Hz, 3H), 2.21-
2.24 (m, 2H), 6.24-6.30 (m, 1H), 6.40 (d, J = 15.9 Hz, 1H),
7.18-7.35 (m, 5H); IR nmax (film) 3024, 2964, 1652, 1598,
1494, 1377, 963, 909, 738 cm-1.
(E)-1-(p-Chlorophenyl)-1-butene (6h)13
1
Colorless oil; H-NMR d 0.89 (t, J = 7.2 Hz, 3H),
2.19-2.21 (m, 2H), 6.20-6.24 (m, 1H), 6.29 (d, J = 15.6 Hz,
1H), 7.12-7.30 (m, 4H); IR nmax (film) 3025, 2964, 1652,
1593, 1490, 1461, 965, 801, 734 cm-1.
(E)-1-Phenyl-2-pentene (6i)14
1
Colorless oil; H-NMR d 1.01 (t, J = 7.4 Hz, 3H),
2.01-2.06 (m, 2H), 3.33 (d, J = 4.0 Hz, 2H), 5.55-5.57 (m,