Alkanes are directly iodinated by perfluoroalkyl iodides by a free- radical chain process initiated by t-BuOOH in acetic acid solution. The initially formed iodoalkanes are reduced back to alkanes by excess t-BuOOH; the rate constant for hydrogen abstraction from t-BuOOH by a primary alkyl radical has been roughly evaluated to be ~ 104 M-1 s-1. Two new procedures for the reductive alkylation of alkenes by t-BuOOH and Pb(OAc)4 are reported. The importance of the polar effects and the rate constants of the key elementary steps involved in these processes is discussed.

(1999). Polar effects in free-radical reactions. The paradox of reduction of alkyl iodides and reductive alkylation of alkenes by strong oxidants (t- BuOOH, Pb(OAc)4) [journal article - articolo]. In JOURNAL OF THE AMERICAN CHEMICAL SOCIETY. Retrieved from https://hdl.handle.net/10446/233272

Polar effects in free-radical reactions. The paradox of reduction of alkyl iodides and reductive alkylation of alkenes by strong oxidants (t- BuOOH, Pb(OAc)4)

Fontana, Francesca;
1999-01-01

Abstract

Alkanes are directly iodinated by perfluoroalkyl iodides by a free- radical chain process initiated by t-BuOOH in acetic acid solution. The initially formed iodoalkanes are reduced back to alkanes by excess t-BuOOH; the rate constant for hydrogen abstraction from t-BuOOH by a primary alkyl radical has been roughly evaluated to be ~ 104 M-1 s-1. Two new procedures for the reductive alkylation of alkenes by t-BuOOH and Pb(OAc)4 are reported. The importance of the polar effects and the rate constants of the key elementary steps involved in these processes is discussed.
articolo
Minisci, Francesco; Fontana, Francesca; Recupero, Francesco; Bravo, Anna; Pagano, Elvira; Rinaldi, Cinzia; Di Luca, Marco; Grossi, Flavia; Bjorsvik, Hans-René
(1999). Polar effects in free-radical reactions. The paradox of reduction of alkyl iodides and reductive alkylation of alkenes by strong oxidants (t- BuOOH, Pb(OAc)4) [journal article - articolo]. In JOURNAL OF THE AMERICAN CHEMICAL SOCIETY. Retrieved from https://hdl.handle.net/10446/233272
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10446/233272
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