Evidences concerning a novel free-radical mechanism for the oxidation of alkanes by aromatic peracids are reported. The mechanism involves hydrogen abstraction from the OH group of peracids by an aroyloxyl radical; the acylperoxyl radical thus generated is responsible for the selective oxidation. The reaction is affected by the presence of oxygen and it is inhibited by TEMPO and by solvents forming hydrogen bonds with peracids. A more simple and effective synthetic procedure has been developed, on the basis of the autoxidation of aliphatic and aromatic aldehydes in the presence of alkanes. It is also shown that the previously reported inertness of alcohols toward peracids must be ascribed to solvent effects, due to the formation of hydrogen bonds; in suitable solvents alcohol oxidation smoothly occurs.

(1996). Radical versus "oxenoid" oxygen insertion mechanism in the oxidation of alkanes and alcohols by aromatic peracids. New synthetic developments [journal article - articolo]. In JOURNAL OF ORGANIC CHEMISTRY. Retrieved from https://hdl.handle.net/10446/232376

Radical versus "oxenoid" oxygen insertion mechanism in the oxidation of alkanes and alcohols by aromatic peracids. New synthetic developments

Fontana, Francesca;
1996

Abstract

Evidences concerning a novel free-radical mechanism for the oxidation of alkanes by aromatic peracids are reported. The mechanism involves hydrogen abstraction from the OH group of peracids by an aroyloxyl radical; the acylperoxyl radical thus generated is responsible for the selective oxidation. The reaction is affected by the presence of oxygen and it is inhibited by TEMPO and by solvents forming hydrogen bonds with peracids. A more simple and effective synthetic procedure has been developed, on the basis of the autoxidation of aliphatic and aromatic aldehydes in the presence of alkanes. It is also shown that the previously reported inertness of alcohols toward peracids must be ascribed to solvent effects, due to the formation of hydrogen bonds; in suitable solvents alcohol oxidation smoothly occurs.
articolo
Bravo, Anna; Bjorsvik, Hans-René; Fontana, Francesca; Minisci, Francesco; Serri, Anna
(1996). Radical versus "oxenoid" oxygen insertion mechanism in the oxidation of alkanes and alcohols by aromatic peracids. New synthetic developments [journal article - articolo]. In JOURNAL OF ORGANIC CHEMISTRY. Retrieved from https://hdl.handle.net/10446/232376
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10446/232376
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