A change in the mechanism of biomimetic oxidation of tertiary amines in response to appropriate structural features of the substrate, emerges from the investigation of the product pattern from N-benzylaziridine under bona fide radical or electron transfer conditions. This substrate is an amine endowed with a high oxidation potential as a result of steric constraint. Consequently, the hydrogen atom transfer route of oxidative N-dealkylation competes favorably with the electron transfer route, which is the mechanism observed for the reaction of conventional tertiary amines with metalloporphyrins and oxygen donors.

The oxidation of N-benzylaziridine induced by iron porphyrin: radical vs. electron transfer mechanism / Cuppoletti, A.; Dagostin, C.; Florea, C.; Galli, Carlo; Gentili, Patrizia; Lanzalunga, Osvaldo; Petride, A.; Petride, H.. - In: CHEMISTRY-A EUROPEAN JOURNAL. - ISSN 0947-6539. - 5:(1999), pp. 2993-2999. [10.1002/(SICI)1521-3765(19991001)5:10<2993::AID-CHEM2993>3.3.CO;2-3]

The oxidation of N-benzylaziridine induced by iron porphyrin: radical vs. electron transfer mechanism.

GALLI, Carlo;GENTILI, Patrizia;LANZALUNGA, Osvaldo;
1999

Abstract

A change in the mechanism of biomimetic oxidation of tertiary amines in response to appropriate structural features of the substrate, emerges from the investigation of the product pattern from N-benzylaziridine under bona fide radical or electron transfer conditions. This substrate is an amine endowed with a high oxidation potential as a result of steric constraint. Consequently, the hydrogen atom transfer route of oxidative N-dealkylation competes favorably with the electron transfer route, which is the mechanism observed for the reaction of conventional tertiary amines with metalloporphyrins and oxygen donors.
1999
01 Pubblicazione su rivista::01a Articolo in rivista
The oxidation of N-benzylaziridine induced by iron porphyrin: radical vs. electron transfer mechanism / Cuppoletti, A.; Dagostin, C.; Florea, C.; Galli, Carlo; Gentili, Patrizia; Lanzalunga, Osvaldo; Petride, A.; Petride, H.. - In: CHEMISTRY-A EUROPEAN JOURNAL. - ISSN 0947-6539. - 5:(1999), pp. 2993-2999. [10.1002/(SICI)1521-3765(19991001)5:10<2993::AID-CHEM2993>3.3.CO;2-3]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/247746
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