Perfluoroalkyl radicals, generated by iodine abstraction from perfluoroalkyl iodides by phenyl radical, react with low selectivity with protonated heteroaromatic bases, due to their electrophilic character and the prevalent enthalpic effect on the reaction. In the presence of alkenes, perfluoroalkyl radicals add very rapidly to the double bond and the polar character of the radical adduct is reversed, allowing the selective substitution of protonated heteroaromatic bases. The mechanism of the reaction and the key role of enthalpic and polar effects are discussed.
(2004). Enthalpic and polar effects in the reactions of perfluoroalkyl radicals: New selective synthetic developments with alkenes and heteroaromatic bases [journal article - articolo]. In JOURNAL OF FLUORINE CHEMISTRY. Retrieved from http://hdl.handle.net/10446/121706
Enthalpic and polar effects in the reactions of perfluoroalkyl radicals: New selective synthetic developments with alkenes and heteroaromatic bases
F. Fontana
2004-01-02
Abstract
Perfluoroalkyl radicals, generated by iodine abstraction from perfluoroalkyl iodides by phenyl radical, react with low selectivity with protonated heteroaromatic bases, due to their electrophilic character and the prevalent enthalpic effect on the reaction. In the presence of alkenes, perfluoroalkyl radicals add very rapidly to the double bond and the polar character of the radical adduct is reversed, allowing the selective substitution of protonated heteroaromatic bases. The mechanism of the reaction and the key role of enthalpic and polar effects are discussed.File | Dimensione del file | Formato | |
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