Abstract
A number of β-phenyl(or benzyl)selanyl- and β-phenylsulfanyl-substituted imines possessing an additional donor nitrogen, oxygen, or sulfur atom were synthesized by reaction of 2-phenylsulfanylethanamine, 2-phenylsulfanylcyclohexanamine, 2-phenylselanylcyclohexanamine, and 2-benzylselanylaniline with salicylaldehyde, 2-pyridinecarbaldehyde, or 2-tert-butylsulfanylbenzaldehyde. The resulting Schiff bases were tested as ligands in the complex formation with nickel(II) and copper(II), and mononuclear (L-H)MCl or LMCl2 coordination compounds were isolated (L = sulfur- or selenium-containing imine). The redox properties of the selenium-containing ligands and complexes were studied by cyclic voltammetry. The complexes were found to undergo reduction of the metal ion in two one-electron steps. The reduction is reversible for copper complexes and irreversible for nickel complexes.
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Jørgensen, A.K., Chem. Rev., 1989, vol. 89, no. 3, p. 431.
Pospisil, P.J., Carsten, D.H., and Jacobsen, E.N., Chem. Eur. J., 1996, vol. 2, no. 8, p. 974.
Bryliakov, K.P. and Talsi, E.P., Inorg. Chem., 2003, vol. 42, no. 22, p. 7258.
Doyle, M.P., Chem. Rev., 1986, vol. 86, no. 5, p. 919.
Evans, D.A., Faul, M.M., and Bilodeau, M.T., J. Am. Chem. Soc., 1994, vol. 116, no. 7, p. 2742.
Evans, D.A., Faul, M.M., and Bilodeau, M.T., J. Org. Chem., 1991, vol. 56, no. 24, p. 6744.
Fukuda, T. and Katsuki, T., Tetrahedron Lett., 1997, vol. 38, no. 19, p. 3435.
Schaus, S.E., Brenalt, J., and Jacobsen, E.N., J. Org. Chem., 1998, vol. 63, no. 2, p. 403.
Kaufman, M.D., Grieco, P.A., and Bougie, D.W., J. Am. Chem. Soc., 1993, vol. 115, no. 24, p. 11 648.
Larrow, J.F. and Jacobsen, E.N., J. Am. Chem. Soc., 1994, vol. 116, no. 26, p. 12 129.
Jacobsen, E.N., Kakiuchi, F., Konsler, R.G., Larrow, J.F., and Tokunaga, M., Tetrahedron Lett., 1997, vol. 38, no. 5, p. 773.
Tokunaga, M., Larrow, J.F., Kakiuchi, F., and Jacobsen, E.N., Science, 1997, vol. 277, no. 8, p. 936.
Leighton, J.L. and Jacobsen, E.N., J. Org. Chem., 1996, vol. 61, no. 1, p. 389.
Martinez, L.E., Leighton, J.L., Carsten, D.H., and Jacobsen, E.N., J. Am. Chem. Soc., 1995, vol. 117, no. 21, p. 5897.
Paddock, R.L. and Nguyen, S.B.T., J. Am. Chem. Soc., 2001, vol. 123, no. 46, p. 11 498.
Darensbourg, D.J. and Holtcamp, M.W., Coord. Chem. Rev., 1996, vol. 153, p. 155.
Butin, K.P., Moiseeva, A.A., Beloglazkina, E.K., Chudinov, Yu.B., Chizhevskii, A.A., Mironov, A.V., Tarasevich, B.N., Lalov, A.V., and Zyk, N.V., Izv. Akad. Nauk, Ser. Khim., 2005, no. 1, p. 169.
Dewar, M.J.S., Healy, E.F., and Stewart, J.J.P., J. Comput. Chem., 1984, vol. 5, no. 4, p. 358.
Chernysheva, A.N., Antipin, R.L., Borisenko, A.A., Beloglazkina, E.K., and Zyk, N.V., Izv. Akad. Nauk, Ser. Khim., 2011, no. 1, p. 189.
Amosova, S.V., Makhaeva, N.A., Martynov, A.V., Potapov, V.A., Steele, B.R., and Kostas, I.D., Synthesis, 2005, no. 10, p. 1641.
Carlans, M.W., Robyn, L.M., and Schiesser, C.H., Org. Biomol. Chem., 2004, vol. 2, no. 18, p. 2612.
Meth-Cohn, O. and Tarnowski, B., Synthesis, 1978, no. 1, p. 56.
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Original Russian Text © A.N. Chernysheva, E.K. Beloglazkina, R.L. Antipin, A.A. Moiseeva, N.V. Zyk, 2013, published in Zhurnal Obshchei Khimii, 2013, Vol. 83, No. 2, pp. 257–264.
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Chernysheva, A.N., Beloglazkina, E.K., Antipin, R.L. et al. New sulfanyl- and selanyl-substituted Schiff bases derived from 2-chalcogenoalkylamines and aromatic aldehydes. Synthesis and complex formation reactions. Russ J Gen Chem 83, 311–318 (2013). https://doi.org/10.1134/S1070363213020138
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DOI: https://doi.org/10.1134/S1070363213020138