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Friedrich, K.; Wallensfels, K. The Chemistry of the Cyano Group; Rappoport, Z., Ed.; Wiley-Interscience: New York, 1970.
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The Chemistry of the Cyano Group
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Friedrich, K.1
Wallensfels, K.2
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4
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(a) Erman, M. B.; Snow, J. W.; Williams, M. J. Tetrahedron Lett. 2000, 41, 6749.
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For examples, see: a
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For examples, see: (a) Sandnya, A. Synthesis 1982, 190.
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Sandnya, A.1
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8
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0031708644
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(b) Feng, J. C.; Lin, G.; Dia, L.; Bian, N. S. Synth. Commun. 1998, 28, 3765.
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2542510395
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(d) Kumar, H. M. S.; Reddy, B. V. S.; Deddy, P. T.; Yadav, J. S. Synthesis 1999, 586.
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Kumar, H.M.S.1
Reddy, B.V.S.2
Deddy, P.T.3
Yadav, J.S.4
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Koshima, H.1
Hamada, M.2
Tani, M.3
Iwasaki, S.4
Sato, F.5
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(g) Srinivas, K. V. N. S.; Mahender, I.; Das, B. Chem. Lett. 2003, 32, 738.
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Srinivas, K.V.N.S.1
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Das, B.3
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15
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0037281055
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and references cited therein
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(i) Sharghi, H.; Sarvari, M. H. Synthesis 2003, 243; and references cited therein.
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Synthesis
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Sharghi, H.1
Sarvari, M.H.2
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16
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33846005816
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Kuo, C. W.; Zhu, J. L.; Wu, J. D.; Chu, C. M.; Yao, C. F.; Shia, K. S. Chem. Commun. 2007, 301.
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Kuo, C.W.1
Zhu, J.L.2
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Chu, C.M.4
Yao, C.F.5
Shia, K.S.6
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17
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34249784322
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2 and PhCH=NOH were obtained as the single stereoisomers. The stereochemistry remains to be determined.
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2 and PhCH=NOH were obtained as the single stereoisomers. The stereochemistry remains to be determined.
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18
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34249777887
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An optimized amount of 3 Å MS was used. It was found that at least 120 mg of 3 Å MS was required for a quantitative conversion of 1.50 mmol of benzaldehyde (1) into benzonitrile 2
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An optimized amount of 3 Å MS was used. It was found that at least 120 mg of 3 Å MS was required for a quantitative conversion of 1.50 mmol of benzaldehyde (1) into benzonitrile (2).
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19
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34249789091
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Satisfactory spectral and LC-MS analytical data were obtained for all products; all known nitriles showed physical and spectral properties identical to those reported in the literature
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Satisfactory spectral and LC-MS analytical data were obtained for all products; all known nitriles showed physical and spectral properties identical to those reported in the literature.
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20
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0033607627
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For the preparation of compound 3, see: Falorni, M.; Giacomelli, G.; Porcheddu, A.; Teddei, M. J. Org. Chem. 1999, 64, 8962.
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For the preparation of compound 3, see: Falorni, M.; Giacomelli, G.; Porcheddu, A.; Teddei, M. J. Org. Chem. 1999, 64, 8962.
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21
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0037068148
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Monica, C.D.1
Randazzo, A.2
Bifulco, G.3
Cimino, P.4
Aquino, M.5
Izzo, I.6
Riccardis, F.D.7
Luigi, G.P.8
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22
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0026031238
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Costello, G. F.; James, R.; Shaw, J. S.; Slater, A. M.; Stutchbury, N. C. J. J. Med. Chem. 1991, 34, 181.
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Costello, G.F.1
James, R.2
Shaw, J.S.3
Slater, A.M.4
Stutchbury, N.C.J.5
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25
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34249786661
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A representative experimental procedure is described for the preparation of benzonitrile (2, To a solution of benzaldehyde (1, 0.2 g, 1.88 mmol) in CH2Cl2 (8 mL, powdered 3 A MS (120 mg, 1.2 equiv of NH2OH·HCl (0.157 g. 2.26 mmol) and 5 equiv of DBU (143 g, 9.42 mmol) were successively added in one portion. The reaction mixture was stirred at r.t. for 10 h, cooled in an ice-water bath to 5°C, and 1.5 equiv of EtOPOCl2 (0.46 g, 2.83 mmol) were added. Then, stirring at r.t. was continued for an additional 5 h. The mixture was then quenched with aq NH4Cl2, extracted with CH2Cl2 and subjected to chromatographic purification on silica gel (15% EtOAc in hexane) to afford 2 in 96% yield (0.186 g, whose spectral data (IR, 1H NMR and 13C NMR) were identical to those of the authentic sample. Benzonitrile(2, IR KBr, 2228, 1701, 1597, 1583, 148
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25 -16.4 (c 0.98, dioxane)}.
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