Oxidative ring-opening of ferrocenylcyclopropylamines to N-ferrocenylmethyl β-hydroxyamides

Authors

Yi Sing Gee, University of WollongongFollow
Neils J. M Goertz, University of Wollongong
Michael G. Gardiner, University of Tasmania
Christopher J. T Hyland, University of WollongongFollow

RIS ID

105717

Publication Details

Gee, Y., Goertz, N. J. M., Gardiner, M. G. & Hyland, C. J. T. (2016). Oxidative ring-opening of ferrocenylcyclopropylamines to N-ferrocenylmethyl β-hydroxyamides. Organic and Biomolecular Chemistry, 14 (8), 2498-2503.

Abstract

The in situ reduction of ferrocenyl cyclopropylimines to the corresponding amines triggers a facile oxidative ring-opening to yield the formal four-electron oxidation products: N-ferrocenylmethyl β-hydroxyamides. This process is believed to proceed via generation of a ferrocinium ion in the presence of air, leading to facile formation of a distonic radical cation that is ultimately trapped by oxygen.