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

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 presenc...

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Published inOrganic & biomolecular chemistry Vol. 14; no. 8; pp. 2498 - 253
Main Authors Gee, Yi Sing, Goertz, Neils J. M, Gardiner, Michael G, Hyland, Christopher J. T
Format Journal Article
Published 16.02.2016
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Summary: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. 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.
Bibliography:Electronic supplementary information (ESI) available. CCDC
For ESI and crystallographic data in CIF or other electronic format see DOI
1434659
10.1039/c5ob02577j
ISSN:1477-0520
1477-0539
DOI:10.1039/c5ob02577j