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

Yi Sing Gee; Neils J.M. Goertz; Michael G. Gardiner; Christopher J.T. Hyland

doi:10.1039/c5ob02577j

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

Yi Sing Gee, Neils J.M. Goertz, Michael G. Gardiner, Christopher J.T. Hyland

Research output: Contribution to journal › Article › Research › peer-review

5 Citations (Scopus)

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.

Original language	English
Pages (from-to)	2498-2503
Number of pages	6
Journal	Organic & Biomolecular Chemistry
Volume	14
Issue number	8
DOIs	https://doi.org/10.1039/c5ob02577j
Publication status	Published - 1 Jan 2016
Externally published	Yes

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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.",

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AU - Goertz, Neils J.M.

AU - Gardiner, Michael G.

AU - Hyland, Christopher J.T.

PY - 2016/1/1

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N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/84983165318

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DO - 10.1039/c5ob02577j

M3 - Article

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JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

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ER -

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

Abstract

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