Abstract
A novel method for the preparation of nitriles of α-chlorocinnamic acid from aldehydes and ketones was proposed. Transformation of carbonyl compounds into hydrazones followed by treatment of the reaction mixture with CCl3CN in the presence of copper chloride(i) yields α-chlorocinnamonitriles.
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A. Yu. Rulev, Usp. Khim., 1998, 67, 317 [Russ. Chem. Rev., 1998, 67 (Engl. Transl.)].
A. V. Shastin, V. N. Korotchenko, V. G. Nenajdenko, and E. S. Balenkova, Izv. Akad. Nauk, Ser. Khim., 1999, 2210 [Russ. Chem. Bull., 1999, 48, 2184 (Engl. Transl.)].
A. V. Shastin, V. N. Korotchenko, V. G. Nenajdenko, and E. S. Balenkova, Tetrahedron, 2000, 56, 6557.
V. N. Korotchenko, A. V. Shastin, V. G. Nenajdenko, and E. S. Balenkova, Tetrahedron, 2001, 57, 7519.
A. V. Shastin, V. N. Korotchenko, V. G. Nenajdenko, and E. S. Balenkova, Izv. Akad. Nauk, Ser. Khim., 2001, 1334 [Russ. Chem. Bull., Ent. Ed., 2001, 50, 1401].
V. N. Korotchenko, A. V. Shastin, V. G. Nenajdenko, and E. S. Balenkova, J. Chem. Soc., Perkin Trans. 1, 2002, 883.
Y. Shen and S. Gao, J. Chem. Soc., Perkin Trans. 1, 1996, 2531.
K. Jahnisch and H. Seeboth, J. Prakt. Chem., 1981, 323, 26.
Y. M. Saunier, R. Danion-Bougot, D. Danion, and R. Carrie, Bull. Soc. Chim. Fr., 1976, 11–12, 1963.
K. Schollberg, H. Schafer, and K. Gewald, J. Prakt. Chem., 1983, 325, 876.
H. W. Moore, F. Mercer, D. Kunert, and P. Albaugh, J. Am. Chem. Soc., 1979, 101, 5435.
V. G. Nenajdenko, V. N. Korotchenko, A. V. Shastin, D. A. Tyurin, and E. S. Balenkova, Izv. Akad. Nauk, Ser. Khim., 2003 1740 [Russ. Chem. Bull., Int. Ed., 2003, 52, 1835].
P. E. Hansen, Prog. Nucl. Magn. Reson. Spectrosc., 1981, 14, 175.
V. G. Nenajdenko, O. N. Lenkova, A. V. Shastin, and E. S. Balenkova, Synthesis, 2004, No. 2.
A. J. Gordon and R. A. Ford, The Chemists Companion. A Handbook of Practical Data, Techniques and References, Wiley—Interscience, New York, 1972.
L. A. Dakin, S. E. Schaus, E. N. Jacobsen, and J. S. Panek, Tetrahedron Lett., 1998, 39, 8947.
V. Gettwert, F. Krebs, and G. Maas, Eur. J. Org. Chem., 1999, 5, 1213.
V. K. Aggarwal, J. G. Ford, R. V. Jones, and R. H. Fieldhouse, Tetrahedron Asymmetry, 1998, 9, 1801.
T. Curtius and A. Lublin, Chem. Ber., 1900, 33, 2464.
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Nenajdenko, V.G., Shastin, A.V., Golubinskii, I.V. et al. New method for the synthesis of α-chlorocinnamonitriles. Russian Chemical Bulletin 53, 228–232 (2004). https://doi.org/10.1023/B:RUCB.0000024853.81460.6a
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DOI: https://doi.org/10.1023/B:RUCB.0000024853.81460.6a