Abstract
Solvent effect on the ratio of the endo and exo isomers formed by the Diels-Alder reaction of cyclopentadiene with acrylic acid esters can be described by multiparameter equations involving solvent polarity and electrophilic solvating power as determining parameters. The solvent polarity parameter Ω based on the stereoisomer ratio in the reaction with methyl acrylate cannot be regarded as a universal measure of solvating power, which was demonstrated using a number of examples.
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Berson, J.A., Hamlet, Z., and Mueller, W.A., J. Am. Chem. Soc., 1962, vol. 84, no. 2, p. 297.
Kosower, E.M., J. Am. Chem. Soc., 1958, vol. 80, no. 13, p. 3253.
Grunwald, E. and Winstein, S., J. Am. Chem. Soc., 1948, vol. 70, no. 10, p. 846.
Smith, S.G., Feinberg, A.R., and Winstein, S., J. Am. Chem. Soc., 1961, vol. 83, no. 4, p. 618.
Reichardt, Ch., Solvents and Solvent Effects in Organic Chemistry, Weinheim: Wiley, 2003, 3rd ed., pp. 178, 280, 294.
Lattes, A., Rico, I., de Savignac, A., and Ahmad-Zadeh Samii, A., Tetrahedron, 1987, vol. 43, no. 7, p. 1725.
Moss, R.A., Whittle, J.R., and Freidenreich, P., J. Org. Chem., 1969, vol. 34, no. 7, p. 2217.
King, J.F. and Pews, R.S., Can. J. Chem., 1965, vol. 43, no. 4, p. 847.
Griffiths, T.R. and Pugh, D.C., Coord. Chem. Rev., 1979, vol. 29, no. 2, p. 129.
Pytela, O., Collect. Czech. Chem. Commun., 1988, vol. 53, no. 7, p. 1333.
Entelis, S.G. and Tiger, R.P., Kinetika reaktsii v zhidkoi faze (Kinetics of Liquid-Phase Reactions), Moscow: Khimiya, 1973.
Reichardt, Ch., Angew. Chem., 1965, vol. 77, no. 1, p. 30.
Blankenburg, B., Fiedler, H., Hampel, M., Hauthal, H.G., Just, G., Kahlert, K., Korn, J., Muller, K.-H., Pritzkow, W., Reinhold, Y., Rullig, M., Sauer, E., Schnurpfeil, D., and Zimmermann, G., J. Prakt. Chem., 1974, vol. 316, no. 5, p. 804.
Corsico Coda, A., Desimoni, G., Ferrari, E., Righetti, P.P., and Tacconi, G., Tetrahedron, 1984, vol. 40, no. 9, p. 1611.
Lassau, C. and Jungers, J.C., Bull. Soc. Chim. Fr., 1968, no. 11, p. 2678.
Abraham, M.H. and Grellier, P.L., J. Chem. Soc., Perkin Trans. 2, 1976, no. 7, p. 1735.
Dvorko, G.F., Ponomareva, E.A., and Kulik, N.I., Usp. Khim., 1984, vol. 53, no. 6, p. 948.
Karpyak, N.M., Makitra, R.G., Marshalok, G.A., and Pal’chikova, O.Ya., Zh. Prikl. Khim., 2006, vol. 74, no. 1, p. 100.
Karpyak, N.M., Makitra, R.G., Marshalok, G.A., Pal’chikova, O.Ya., and Yatchishin, I.I., Russ. J. Gen. Chem., 2005, vol. 75, no. 11, p. 1712.
Koppel, I.A. and Palm, V.A., Advances in Linear Free Energy Relationships, Chapman, N.B. and Shorter, J., London: Plenum, 1972, p. 203.
Brownstein, S., Can. J. Chem., 1960, vol. 38, no. 11, p. 1590.
Mayer, U., Gutmann, V., and Gerger, W., Monatsh. Chem., 1976, vol. 106, no. 6, p. 1235.
Herbrandson, H.F. and Neufeld, F.R., J. Org. Chem., 1966, vol. 31, no. 4, p. 1140.
Griffiths, T.R. and Pugh, D.C., J. Solution Chem., 1979, vol. 8, no. 3, p. 247.
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Original Russian Text © N.M. Karpyak, R.G. Makitra, G.A. Marshalok, E.Ya. Pal’chikova, 2008, published in Zhurnal Obshchei Khimii, 2008, Vol. 78, No. 1, pp. 111–117.
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Karpyak, N.M., Makitra, R.G., Marshalok, G.A. et al. Solvent effect on the stereoselectivity in cycloaddition of cyclopentadiene to unsaturated esters. Invalidity of the solvent polarity parameter Ω. Russ J Gen Chem 78, 106–111 (2008). https://doi.org/10.1134/S1070363208010180
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DOI: https://doi.org/10.1134/S1070363208010180