C. Kuang et al. / Tetrahedron 58 (2002) 1491±1496
1495
4.1.10. (E)-b-Bromo-3-nitrostyrene (2j).27,29 The crude
product was puri®ed by silica gel column chromatography
eluted with 40% EtOAc in hexane; mp70±71 8C; IR (nujol)
Hamaoka, T.; Ravindran, N.; Subrahmanyam, C.; Somayaji,
V.; Bhat, N. G. J. Org. Chem. 1989, 54, 6075±6079.
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(e) Masuda, Y.; Hoshi, M.; Arase, A. J. Chem. Soc., Perkin
Trans. 1 1992, 2725±2726. (f) Stewart, S. K.; Whiting, A.
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1
1616, 1524, 1352, 937 cm21; H NMR d 6.99 (1H, d, J
14.2 Hz), 7.18 (1H, d, J14.2 Hz), 7.52 (1H, t, J7.6 Hz),
7.62 (1H, dd, J1.3 and 7.6 Hz), 8.7 (1H, d, J1.7 Hz),
8.3±8.7 (1H, m); 13C NMR d 110.10, 120.68, 122.79,
129.79, 131.81, 134.99, 137.47, 148.80; EIMS m/z 229
((M12)1, 45), 227 (M1, 48), 183 (15), 181 (16), 102
(100); HRMS Calcd for C8H679BrNO2; m/z 226.9581.
Found m/z 226.9571.
5. Miller, R. B.; McGarvey, G. J. Org. Chem. 1978, 43, 4424±
4431.
4.1.11. (E/Z)-1-Bromo-4-phenylbuta-1,3-diene (2k).13i IR
(nujol) 1691, 1448, 974, 741 cm21; 1H NMR d 6.23 (0.27H,
d, J6.9 Hz, (Z)), 6.42 (0.73H, d, J13.2 Hz, (E)), 6.5±6.8
(2H, m), 6.87 (0.73H, dd, J10.2 and 13.5 Hz, (E)), 7.11
(0.27H, ddd, J1.0, 9.9 and 13.5 Hz, (Z)), 7.2±7.5 (5H, m);
EIMS m/z 210 ((M12)1, 3), 208 (M1, 3), 129 (75), 128
(100), 102 (26); HRMS Calcd for C10H979Br; m/z
207.9887. Found m/z 207.9893.
6. (a) Takai, K.; Nitta, K.; Utimoto, K. J. Am. Chem. Soc. 1986,
108, 7408±7410. (b) Takai, K.; Ichiguchi, T.; Hikasa, S.
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7. (a) Harada, T.; Katsuhira, T.; Oku, A. J. Org. Chem. 1992, 57,
5805±5807. (b) Harada, T.; Katsuhira, T.; Hara, D.; Kotani,
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4897±4907.
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4.1.12. (E/Z)-1-Bromo-2-cyclohexylethene (2l).5,30 IR
9. (a) Lipshutz, B. H.; Keil, R.; Ellsworth, E. L. Tetrahedron
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Â
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1
(neat) 1619, 942, 707 cm21; H NMR d 1.0±1.4 (5H, m),
1.6±1.8 (5H, m), 1.9±2.1 (0.68H, m, E), 2.4±2.6 (0.32H,
m), 5.92 (0.32H, m, Z), 5.92 (0.32H, dd, J6.9 and 8.9 Hz,
Z), 5.99 (0.68H, dd, J1.0 and 13.5 Hz, E), 6.04 (0.32H, dd,
J1.0 and 6.9 Hz, Z), 6.14 (0.68H, dd, J7.3 and 13.5 Hz,
E); 13C NMR d 25.54 (Z), 25.72 (E), 25.88 (E and Z), 31.55
(Z), 32.24 (E), 38.79 (Z), 41.76 (E), 103.08 (E), 105.42 (Z),
140.14 (Z), 143.69 (E); EIMS m/z 190 ((M12)1, 7), 188
(M1, 8), 109 (100), 67 (94); HRMS Calcd for C8H1379Br;
m/z 188.0200. Found m/z 188.0194.
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Bhandari, A. Tetrahedron Lett. 1994, 35, 4669±4672.
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6003±6006. (e) Huang, X.; Wang, J.-H.; Yang, D.-Y.
J. Chem. Soc., Perkin Trans. 1 1999, 673±674.
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4.1.13. (E/Z)-1-Bromonon-1-ene (2m).31 IR (neat) 1623,
1
940, 721 cm21; H NMR d 0.85±0.95 (3H, m), 1.2±1.5
(10H, m), 1.99±2.07 (1.16H, m, E), 2.15±2.22 (0.84H, m,
Z), 6.00 (0.58H, J1.3 and 13.5 Hz, E), 6.02±6.23 (1.42H,
m); EIMS m/z 206 ((M12)1, 20), 204 (M1, 21), 123 (56),
83 (61), 81 (71), 69 (100), 43 (96), 41 (77); HRMS Calcd for
C9H1779Br; m/z 204.0513. Found m/z 204.0500.
11. Ranu, B. C.; Samanta, S.; Guchhait, S. K. J. Org. Chem. 2001,
66, 4102±4103.
Á
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J. Organomet. Chem. 2001, 624, 131±135.
13. (a) Jones, A. S.; Verhelst, G.; Walker, R. T. Tetrahedron Lett.
1979, 4415±4418. (b) Barton, D. H. R.; Crich, D.;
Motherwell, W. B. Tetrahedron Lett. 1983, 24, 4979±4982.
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(f) Chowdhury, S.; Roy, S. Tetrahedron Lett. 1996, 37, 2623±
2624. (g) Chowdhury, S.; Roy, S. J. Org. Chem. 1997, 62,
199±200. (h) Naskar, D.; Chowdhury, S.; Roy, S. Tetrahedron
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(k) You, H.-W.; Lee, K.-J. Synlett 2001, 105±107. (l) Sinha,
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Acknowledgements
This work was supported by a Grant-in-Aid for Exploratory
Research (No. 13875171) from Japan Society for the
Promotion of Science. We would like to thank S. Oka,
M. Kiuchi, Y. Takihata and N. Hazama (Center for Instru-
mental Analysis, Hokkaido University) for their assistance
in measurement of mass spectra.
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