3 P. T. Anastas, L. B. Bartlett, M. M. Kirchhoff and T. C. Williamson,
Catal. Today, 2000, 55, 11–22.
12 V. M. Potapov, E. G. Solozhenko and G. V. Panova, Zhurnal Obshchei
Khimii, 1984, 54, 662–665.
13 W. Chen and L. Shi, Catal. Commun., 2008, 9, 1079–1081.
14 C. B. Ranu and T. Mandal, Aust. J. Chem., 2007, 60, 223–227.
15 M. Menand and V. Dalla, Synlett, 2005, 95–98.
16 A. Ziyaei-Halimehjani and R. M. Saidi, Tetrahedron Lett., 2008, 49,
1244–1248.
17 L. F. Cason and C. C. Wanser, J. Am. Chem. Soc., 1951, 73, 142–145.
18 C.-M. Chu, Z. Tu, P. Wu, C.-C. Wang, J.-T. Liu, C.-W. Kuo, Y.-H.
Shin and C.-F. Yao, Tetrahedron, 2009, 65, 3878–3885.
19 b-Nitrostyrenes have been synthesized using a modified procedure
(Ref. 20). In a typical procedure, a mixture of 3-nitrobenzaldehyde
(2.267 g, 15 mM), nitromethane (6 mL, 110 mM) and ammonium
acetate (0.4 g, 5.2 mM) in glacial acetic acid (40 mL) was heated
under reflux for 8 h. Then the hot solution was poured into 400 mL
of ice-cold water in a beaker. Immediately the product began to
precipitate out. To get the complete precipitation, the beaker was
kept in refrigerator for 4 h. The precipitate was filtered under reduced
pressure, washed with water and dried under vacuum to afford 2.84 g
(97.6%) of pure 3-nitro-b-nitrostyrene (2b).
20 (a) X. A. Dominguez, J. Slim and A. Elizondo, J. Am. Chem. Soc.,
1953, 75, 4581–4582; (b) J.-T. Liu and C.-F. Yao, Tetrahedron Lett.,
2001, 42, 6147–6150.
21 (a) O. Dann and E. F. Holler, Chem. Ber., 1949, 82, 76; (b) O. Schales
and H. A. Graefe, J. Am. Chem. Soc., 1952, 74, 4486; (c) K. Zee-
Cheng and C. Cheng, J. Med. Chem., 1969, 12, 157; (d) G. W. Kabalka
and R. S. Varma, Org. Prep. Proced. Int., 1987, 19, 283–328.
4 (a) B. M. Trost and A. C. Lavoie, J. Am. Chem. Soc., 1983, 105, 5075–
5090; (b) R. D. Miller and R. Hassig, Tetrahedron Lett., 1985, 26,
2395–2398; (c) H. Mizuno, K. Domon, K. Masuya, K. Tanino and
I. Kuwajima, J. Org. Chem., 1999, 64, 2648–2656; (d) D. Enders and
U. Reinhold, Tetrahedron: Asymmetry, 1997, 8, 1895–1946; (e) A.
Cordova, Acc. Chem. Res., 2004, 37, 102–112.
5 (a) D. Lucet, T. Le Gall and C. Mioskowski, Angew. Chem., Int.
Ed., 1998, 37, 2580–2627; (b) D. Lucet, L. Toupet, T. Le Gall
and C. Mioskowski, J. Org. Chem., 1997, 62, 2682–2683; (c) P. H.
O’Brien, D. R. Sliskovic, C. J. Blankley, B. Roth, M. W. Wilson,
K. L. Hamelehle, B. R. Krause and R. L. Stanfield, J. Med. Chem.,
1994, 37, 1810–1822.
6 (a) F. Fini, V. Sgarzani, D. Pettersen, R. P. Herrera, L. Bernardi and
A. Ricci, Angew. Chem., Int. Ed., 2005, 44, 7975–7578; (b) E. Foresti,
G. Palmieri, M. Petrini and R. Profeta, Org. Biomol. Chem., 2003,
1, 4275–4281; (c) R. Ballini and M. Petrini, Tetrahedron, 2004, 60,
1017–1047; (d) H. W. Pinnick, Org. React., 1990, 38, 655–792.
7 M. Jafarpour, A. Rezaeifard and M. Aliabadi, Letters in Organic
Chemistry, 2009, 6, 94–99.
8 J. S. Yadav, A. R. Reddy, Y. G. Rao, A. V. Narsaiah and B. V. S.
Reddy, Synthesis, 2007, 22, 3447–3450.
9 A. S. Mahasneh, Basic Sci. Engg., 2004, 13, 79–86.
10 P. A. Sarathi, C. Gnanasekaran and A. Shunmugasundaram, Bull.
Korean Chem. Soc., 2008, 29, 790–794.
11 P. Kotrusz and B. Toma, Molecules, 2006, 11, 197–205.
282 | Green Chem., 2011, 13, 276–282
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