The homolytic benzylation of protonated 4-cyanopyridine, quinoline, 2-methyl- and 4-methylquinoline, isoquinoline, and quinoxaline is investigated. The great influence of the polar effect and of the reversibility of the addition of the benzyl radical on the reaction selectivity is discussed. It is put forward the hypothesis that the HSAB principle can be extended to free-radical reactions when the polar effect is the dominant factor. © 1986, American Chemical Society. All rights reserved.
(1986). Polar Effects in Free-Radical Reactions. Selectivity and Reversibility in the Homolytic Benzylation of Protonated Heteroaromatic Bases [journal article - articolo]. In JOURNAL OF ORGANIC CHEMISTRY. Retrieved from https://hdl.handle.net/10446/231753
Polar Effects in Free-Radical Reactions. Selectivity and Reversibility in the Homolytic Benzylation of Protonated Heteroaromatic Bases
Fontana, F.;
1986-01-01
Abstract
The homolytic benzylation of protonated 4-cyanopyridine, quinoline, 2-methyl- and 4-methylquinoline, isoquinoline, and quinoxaline is investigated. The great influence of the polar effect and of the reversibility of the addition of the benzyl radical on the reaction selectivity is discussed. It is put forward the hypothesis that the HSAB principle can be extended to free-radical reactions when the polar effect is the dominant factor. © 1986, American Chemical Society. All rights reserved.| File | Dimensione del file | Formato | |
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