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31+G(d,p) level of theory. All the calculations were performed
using the Gaussian 09 package.32
(b) J.-H. Choi, B.-C. Lee, H.-W. Lee and I. Lee, J. Org. Chem.,
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Synthetized product
To a stirred solution of 1-uoro-2,4-dinitrobenzene (1.0 g, 5.4
mmol) in ethanol (20 mL), containing potassium carbonate
(1.49 g, 10.8 mmol), was added morpholine (468 mg, 5.4 mmol)
and the reaction mixture was reuxed for 30 min. The ethanol
was evaporated, the residue was extracted with ethyl acetate (25
mL) and the organic layer was dried and concentrated. The
crude product was puried by ash chromatography on silica
16 O. Banjoko and I. A. Babatunde, Tetrahedron, 2004, 60, 4645.
´
17 (a) R. Ormazabal-Toledo, R. Contreras, R. A. Tapia and
´
P. R. Campodonico, Org. Biomol. Chem., 2013, 11, 2302; (b)
´
´
R. Ormazabal-Toledo, R. Contreras and P. R. Campodonico,
gel (ethyl acetate–hexane 1 : 1) to give N-(2,4-dinitrophenyl)
J. Org. Chem., 2013, 78, 1091.
1
ꢃ
ꢃ
morpholine (1.2 g, 88%), mp 120–121 C (Lit. 117–118 C). H-
NMR (200 MHz, CDCl3) d: 3.28 (t, J ¼ 4.7 Hz, 4H), 3.87 (t, J ¼
4.7 Hz, 4H), 7.13 (d, J ¼ 9.3 Hz, 1H), 8.28 (dd, J ¼ 9.3, 2.8 Hz,
1H), 8.69 (d, J ¼ 2.8 Hz, 1H); 13C-NMR (50.4 MHz, CDCl3) d: 50.9,
´
´
18 R. Contreras, R. Ormazabal-Toledo and P. R. Campodonico,
in Arene Chemistry: Reaction Mechanisms and Methods for
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66.1, 119.2, 123.9, 128.4, 138.4, 138.9, 149.3. FT-IR (Nujol) 3115,
1610, 1590, 1530, 1330 cmꢁ1
.
33
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Acknowledgements
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This work was supported by project RC-130006 CILIS, granted
by fondo de Innovacion para la competitividad Del Ministerio
de Economia, Fomento y Turismo, Chile and Fondecyt Grants
1150759. J. A.-E. thanks CONICYT of Chile for a doctoral
fellowship.
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99328 | RSC Adv., 2015, 5, 99322–99328
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