The Oxidation of N-Benzylaziridine Catalyzed by Iron Porphyrin: Radical versus Electron Transfer Mechanism
✍ Scribed by Andrea Cuppoletti; Claudio Dagostin; Cristina Florea; Carlo Galli; Patrizia Gentili; Osvaldo Lanzalunga; Aurica Petride; Horia Petride
- Publisher
- John Wiley and Sons
- Year
- 1999
- Tongue
- English
- Weight
- 149 KB
- Volume
- 5
- Category
- Article
- ISSN
- 0947-6539
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✦ Synopsis
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.