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R. Ballini et al.
SHORT PAPER
Table 2 Spectroscopic Data of Dinitro Compounds 5a–k (continued)
Compound IR (KBr)a
(cm–1)
1H NMR (200 MHz, CDCl3):b d (ppm), J (Hz)
13C NMR (75 MHz,
EI–MS (70 eV): m/z
CDCl3):b d (ppm), J (Hz)
5g
1376, 1560,
1654, 3034
4.22–4.33 (m, 1 H), 4.69–4.82 (m, 4 H), 7.17–7.20 42.0, 77.0, 127.6, 129.3,
(m, 2 H), 7.22–7.38 (m, 3 H) 129.7, 134.5
30, 39, 51, 65, 77, 91, 105,
117 (100), 133, 163, 210
5h
1380, 1552
4.32–4.46 (m, 1 H), 4.72–4.88 (m, 4 H), 7.38 (d, 41.6, 76.5, 126.7, 126.8,
30, 39, 51, 63, 77, 91, 103,
J = 8.2 Hz, 2 H), 7.65 (d, J = 8.2 Hz, 2 H)
126.9, 127.0, 128.2, 138.4 117, 133, 151, 165 (100),
173, 185, 201, 212, 231, 259
5i
5j
1379, 1543,
1615
3.78 (s, 3 H), 4.21–4.29 (m, 1 H), 4.71 (d, J = 1.8 41.3, 55.4, 77.1, 115.0,
Hz, 2 H), 4.75 (d, J =1 .8 Hz, 2 H), 6.87 (d, J = 8.8 126.0, 128.7, 160.1
Hz, 2 H), 7.14 (d, J = 8.8 Hz, 2 H)
30, 39, 51, 65, 77, 91, 103,
121, 133 (100), 147, 164,
193, 240
1376, 1560,
1654, 3034
4.40–4.59 (m, 1 H), 5.01–5.27 (m, 4 H), 7.40 (dd, 40.5, 77.1, 124.6, 132.6,
30, 39, 51, 65, 78, 91, 106,
118 (100), 134, 211
J = 7.7, 4.8 Hz, 1 H), 7.92 (dt, J = 8.1, 2.0 Hz, 1
H), 8.55 (dd, J = 4.7, 1.5 Hz, 1 H), 8.70 (d, J = 2.1
Hz, 1 H)
135.9, 150.6, 150.7
5k
1377, 1563
4.37–4.54 (m, 1 H), 4.81 (d, J = 7.0 Hz, 4 H),
6.28–6.31 (m, 1 H), 6.33–6.39 (m, 1 H), 7.41 (t,
J = 0.73 Hz, 1 H)
36.0, 74.7, 109.0, 111.0,
143.6, 147.3
30, 39, 55, 65, 79 (100), 94,
107, 153, 200
a IR for the compounds 5i, 5j and 5k were performed in nujol.
b 1H and 13C NMR for the compounds 5f and 5j were recorded in CD3COCD3.
(8) (a) Ballini, R.; Bosica, G.; Gigli, F. Tetrahedron 1998, 54,
7573. (b) Ballini, R.; Barboni, L.; Bosica, G.; Filippone, P.;
Peretti, S. Tetrahedron 2000, 56, 4095. (c) Ballini, R.; Bigi,
F.; Conforti, M. L.; De Santis, D.; Maggi, R.; Oppici, G.;
Sartori, G. Catal. Today 2000, 60, 305. (d) Ballini R.,
Bosica G., Conforti M. L., Maggi R., Mazzacani A., Righi
P., Sartori G.; Tetrahedron; 2001, 57: 1395. (e) Ballini R.,
Bosica G., Fiorini D., Gil M. V., Petrini M.; Org. Lett.; 2001,
3: 1265. (f) Ballini, R.; Barboni, L.; Bosica, G.; Fiorini, D.;
Gil, M. V.; Petrini, M. Tetrahedron 2001, 57, 6079.
(9) Derri Alcántara, M.-P.; Cabera Escribano, F.; Gómez-
Sánchez, A.; Diánez, M. J.; Estrada, M. D.; López-Castro,
A.; Pérez-Garrido, S. Synthesis 1996, 64.
Acknowledgment
The work was carried out in the framework of the National Project
‘Il Mezzo Acquoso nelle Applicazioni Sintetiche dei Nitrocomposti
Alifatici’ supported by the Ministero dell’Università e della Ricerca
Scientifica e Tecnologica, Rome, Italy.
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Synthesis 2004, No. 12, 1938–1940 © Thieme Stuttgart · New York