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

journal contribution
posted on 2023-05-18, 18:17 authored by Gee, YS, Goertz, NJM, Michael GardinerMichael Gardiner, Hyland, CJT

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

History

Publication title

Organic and Biomolecular Chemistry

Volume

14

Issue

8

Pagination

2498-2503

ISSN

1477-0520

Department/School

School of Natural Sciences

Publisher

Royal Society of Chemistry

Place of publication

United Kingdom

Rights statement

Copyright 2016 The Royal Society of Chemistry

Repository Status

  • Restricted

Socio-economic Objectives

Organic industrial chemicals (excl. resins, rubber and plastics)

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