B. Das et al. / Tetrahedron 60 (2004) 8357–8361
8361
131.2, 130.1, 129.5, 61.8, 30.0, 14.5; m/z (%) 306 (MC$, 1),
Acknowledgements
304 (MC$,4), 302 (MC$, 3), 223 (MCKBr, 37), 151 (50),
149 (38), 115 (100). Anal. Calcd for C12H12O2ClBr: C,
63.55%; H, 3.96%. Found: C, 63.27%; H, 3.85%.
The authors thank CSIR and UGC, New Delhi for financial
assistance. They are also thankful to Dr. B. Venkataiah for
his helpful discussion.
4.3.9. Ethyl-(2Z)-3-(4-chlorophenyl)-2-(iodomethyl)-
propenoate (3g). Brown oil; nmax (KBr) 2975, 1717,
1634, 1445, 1274, 837, 767 cmK1; dH (CDCl3, 200 MHz)
7.84 (1H, s), 7.54 (2H, d, JZ8.0 Hz), 7.38 (2H, d, JZ
8.0 Hz), 4.22 (2H, s), 4.20 (2H, q, JZ7.0 Hz), 1.25 (3H, t,
JZ7.0 Hz); m/z (%) 225 (MC$KI, 48), 223 (MC$KI, 48),
151 (46), 149 (29), 115 (100). Anal. Calcd for C12H12O2ClI:
C, 41.14%; H, 3.42%. Found: C, 40.88%; H, 3.39%.
References and notes
1. (a) Baylis, A. B.; Hillman, M. E. D. German Patent 2155113,
1972; Chem. Abstr. 1972, 77, 34174q. (b) Basavaiah, D.; Rao,
A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811 and
references cited therein.
2. (a) Hoffmann, H. M. R.; Rabe, J. Angew. Chem., Int. Ed. Engl.
1985, 24, 94. (b) Buchholz, R.; Hoffmann, H. M. R. Helv.
Chim. Acta 1991, 74, 1213. (c) Basavaiah, D.; Bakthadoss, M.;
Pandiaraju, S. J. Chem. Soc., Chem. Commun. 1998, 1639.
3. (a) Drewes, S. E.; Emslie, N. D. J. Chem. Soc. Perkin Trans. 1
1982, 2079. (b) Ameer, F.; Drewes, S. E.; Emsile, N. D.; Kaye,
P. T.; Mann, R. L. J. Chem. Soc. Perkin Trans. 1 1983, 2293.
(c) Ameer, F.; Drewes, S. E.; Houston-McMillan, M. S.; Kaye,
P. T. J. Chem. Soc. Perkin Trans. 1 1985, 1143. (d) McFadden,
H. G.; Harris, R. L. N.; Jenkins, C. I. D. Aust. J. Chem. 1989,
42, 301. (e) Chavan, S. P.; Ethiraj, K. S.; Kamat, S. K.
Tetrahedron Lett. 1997, 38, 7415. (f) Goldberg, O.; Dreiding,
A. S. Helv. Chim. Acta 1976, 59, 1904. (g) Rabe, J.; Hoffmann,
H. M. R. Angew. Chem., Int. Ed. Engl. 1983, 22, 795.
(h) Hoffmann, H. M. R.; Rabe, J. J. Org. Chem. 1985, 50,
3049. (i) Das, B.; Banerjee, J.; Ravindranath, N.; Venkataiah,
B. Tetrahedron Lett. 2004, 45, 2425–2426. (j) Yadav, J. S.;
Reddy, B. V. S.; Madan, C. New J. Chem. 2001, 25, 1114.
4. Onaka, M.; Sugita, K.; Izumi, Y. J. Org. Chem. 1989, 54,
1116.
4.3.10. Ethyl-(2Z)-2-(bromomethyl)-3-(4-methoxy-
phenyl)-propenoate (2h). Yellow oil; nmax (KBr) 2932,
1704, 1623, 1457, 1236, 745 cmK1; dH (CDCl3, 200 MHz)
7.66 (1H, s), 7.42 (2H, d, JZ8.0 Hz), 6.83 (2H, d, JZ
8.0 Hz), 4.28 (2H, s), 4.22 (2H, q, JZ7.0 Hz), 3.80 (3H, s),
1.23 (3H, t, JZ7.0 Hz); m/z (%) 300 (MC$, 6) 298 (MC$, 6),
219 (MCKBr, 14), 189 (17), 160 (24), 135 (21), 91 (38).
Anal. Calcd for C13H15O3Br: C, 52.17%; H, 5.01%. Found:
C, 51.82%; H, 4.95%.
4.3.11. Ethyl-(2Z)-2-(iodomethyl)-3-(4-methoxyphenyl)-
propenoate (3h). Brown oil; nmax (KBr) 2937, 1705, 1630,
1448, 1242, 750 cmK1; dH (CDCl3, 200 MHz) 7.68 (1H, s),
7.50 (2H, d, JZ8.0 Hz), 6.98 (2H, d, JZ8.0 Hz), 4.28 (2H,
q, JZ7.0 Hz), 4.24 (2H, s), 3.82 (3H, s), 1.22 (3H, s); m/z
(%) 219 (MCKI, 9), 189 (13), 160 (20), 135 (23), 91 (31).
Anal. Calcd for C13H15O3I: C, 45.08%; H, 4.33%. Found: C,
44.84%; H, 4.29%.
4.3.12. (2E)-2-(Bromomethyl)-3-(3-nitrophenyl)-pro-
penenitrile (2j). White solid, mp 54–55 8C; nmax (KBr)
2923, 2352, 1686, 1530, 1348, 1218, 772 cmK1; dH (CDCl3,
200 MHz) 8.45 (1H, s), 8.32 (1H, d, JZ8.0 Hz), 8.28 (1H, d,
JZ8.0 Hz), 7.67 (1H, t, JZ8.0 Hz), 7.22 (1H, s), 4.18
(2H,s); m/z (%) 268 (MC$, 3) 266 (MC$, 3), 187 (MCKBr,
49), 149 (27), 141 (100), 115 (18). Anal. Calcd for
C10H7N2O2Br: C, 44.94%; H, 2.62%. Found: C, 44.68%;
H, 2.58%.
5. Buchholz, R.; Hoffmann, H. M. R. Helv. Chim. Acta 1991, 74,
1213.
6. Larson, G. L.; de kaifer, C. F.; Seda, R.; Torres, L. E.;
Ramirez, J. R. J. Org. Chem. 1984, 49, 3385.
7. Basavaiah, D.; Sarma, P. K. S.; Bhavani, A. K. D. J. Chem.
Soc., Chem. Commun. 1994, 1091.
8. Baraldi, P. G.; Guarneri, M.; Pollini, G. P.; Simoni, D.; Barco,
A.; Benetti, S. J. Chem. Soc., Perkin Trans. 1 1984, 2501.
9. Tanaka, K.; Yamagishi, N.; Tanikaga, R.; Kaji, A. Bull. Chem.
Soc. Jpn 1979, 52, 3619.
4.3.13. (2E)-2-(Iodomethyl)-3-(3-nitrophenyl)-propene-
nitrile (3j). Yellow solid, mp 120–121 8C; nmax (KBr)
2925, 2354, 1686, 1534, 1348, 1218, 771 cmK1; dH (CDCl3,
200 MHz) 8.43 (1H, s), 8.28 (1H, d, JZ8.0 Hz), 8.24 (1H, d,
JZ8.0 Hz), 7.66 (1H, t, JZ8.0 Hz), 7.22 (1H, s), 4.21
(2H,s); dC (CDCl3, 300 MHz) 143.3, 134.0, 133.7, 130.2,
125.4, 124.4, 121.5, 116.0, 115.1, 29.6; m/z (%) 187 (MCK
I, 56), 149 (24), 141 (100), 115 (17). Anal. Calcd for
C10H7N2O2I: C, 38.21%; H, 2.22%. Found: C, 38.01%; H,
2.19%.
10. Minami, I.; Yahara, M.; Shimizu, I.; Tsuji, J. J. Chem. Soc.,
Chem. Commun. 1986, 118.
11. Oda, M.; Yamamura, A.; Watabe, T. Chem. Lett. 1979, 1427.
12. Matsuda, I.; Okada, H.; Izumi, Y. Bull. Chem. Soc. Jpn 1983,
56, 528.
13. Boche, G.; Buckl, K.; Martens, D.; Schneider, D. R.
Tetrahedron Lett. 1979, 4967.
14. Eagen, M. C.; Cromwell, N. H. J. Org. Chem. 1974, 39, 911.
15. Breton, G. W. J. Org. Chem. 1997, 62, 8952.
16 Gruiec, A.; Poucaud, A. New J. Chem. 1991, 15, 943.