Abstract
The regioselectivity of free radical attack on olefins is considered with respect to the correspondence between energy components in the Morokuma scheme and their analogs in the orbital scheme (FMO approximation) in terms of ambivalence of radicals and the effectiveness of reactant deformation, with the purpose of fitting a CT model.
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Literature cited
K. Kitaura and K. Morokuma, Int. J. Quantum Chem.,10, No. 2, 325–331 (1976).
S. Nagase and K. Morokuma, J. Am. Chem. Soc.,100, No. 6, 1666–1672 (1978).
S. V. Volovik, G. G. Dyadyusha, and V. I. Staninets, Teor. Éksp. Khim.,23, No. 2, 135–148 (1987).
S. V. Volovik, G. G. Dyadyusha, and V. I. Staninets, Regioselectivity and Reactivity of Free Radicals in Addition and Aromatic Substitution Reactions [in Russian], Naukova Dumka, Kiev (1988).
S. V. Volovik, G. G. Dyadyusha, and N. S. Zefirov, Teor. Éksp. Khim.,26, No. 4, 413–421 (1990).
S. Nagase and W. C. Kern, J. Am. Chem. Soc.,101, No. 10, 2544–2549 (1979).
R. Arnaud, Y. Ellinger, K. Subra, and J. Douady, J. Mol. Struct. Theochem.,110, 203–218 (1984).
R. Arnaud, R. Subra, V. Barone, et al., J. Chem. Soc. Perkin Trans. II, No. 13, 1517–1524 (1986).
A. Bottoni, J. Fossey, and D. Lefort, Mol. Phys. Chem.Biol.,3, 173–219 (1989).
F. Delbecq, D. Ilavsky, N. T. Ahn, and J. M. Lefour, J. Am. Chem. Soc.,107, No. 6, 1623–1631 (1985).
E. Canadell, O. Eisenstein, G. Ohanessian, and J. M. Poblet, J. Phys. Chem.,89, No. 22, 4856–4861 (1985).
K. Houk, M. Paddon-Row, D. Spellmeyer, et al., J. Org. Chem.,51, No. 15, 2874–2879 (1986).
K. Fukui, Angew. Chem.,94, No. 11, 852–861 (1982).
N. D. Epiotis, W. Cherry, S. Shaik, et al., Top. Curr. Chem.,70, 1–250 (1977).
S. Shaik and E. Canadell, J. Am. Chem. Soc.,112, No. 4, 1446–1452 (1990).
Additional information
Institute of Organic Chemistry, Academy of Sciences of the Ukrainian SSR Kiev. Translated from Teoreticheskaya i Éxperimental Khimiya, Vol. 27, No. 4, pp. 474–478, July–August, 1991. Original article submitted March 14, 1991.
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Volovik, S.V., Staninets, V.I. Analysis of regioselectivity of free radical addition to olefins by the Morokuma scheme. Theor Exp Chem 27, 414–417 (1991). https://doi.org/10.1007/BF01372519
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DOI: https://doi.org/10.1007/BF01372519