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


Gee, YS and Goertz, NJM and Gardiner, MG and Hyland, CJT, Oxidative ring-opening of ferrocenylcyclopropylamines to N-ferrocenylmethyl β-hydroxyamides, Organic and Biomolecular Chemistry, 14, (8) pp. 2498-2503. ISSN 1477-0520 (2016) [Refereed Article]

Copyright Statement

Copyright 2016 The Royal Society of Chemistry

DOI: doi:10.1039/c5ob02577j


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.

DOI for erratum: 10.1039/c6ob90061e

Item Details

Item Type:Refereed Article
Keywords:catalysis, organometallic
Research Division:Chemical Sciences
Research Group:Inorganic chemistry
Research Field:Transition metal chemistry
Objective Division:Manufacturing
Objective Group:Industrial chemicals and related products
Objective Field:Organic industrial chemicals (excl. resins, rubber and plastics)
UTAS Author:Gardiner, MG (Associate Professor Michael Gardiner)
ID Code:107800
Year Published:2016
Web of Science® Times Cited:5
Deposited By:Chemistry
Deposited On:2016-03-24
Last Modified:2018-03-14

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