Conclusions
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1.
A mechanism was proposed for aromatic nucleophilic substitution, which consists in attack of the nucleophile on the substituted bond, with electron transfer to the aromatic substrate and the formation of a pair of free radicals.
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2.
The probability of the free radicals recombining to the σ-complex decreases with increase in the activity of the nucleophile and the acceptor capacity of the aromatic substrate.
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3.
The theory was expressed that the formation of free radicals is possible in the coordinated reactions that are forbidden because of the symmetry via one-electron transfer as the result of the convergence of the levels of the boundary orbitals of the reactants.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1160–1163, May, 1976.
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D'yachenko, A.I., Ioffe, A.I. Mechanism of aromatic nucleophilic substitution. Russ Chem Bull 25, 1129–1132 (1976). https://doi.org/10.1007/BF00922008
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DOI: https://doi.org/10.1007/BF00922008