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Issue 92, 2017
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Oxaziridine cleavage with a low-valent nickel complex: competing C–O and C–N fragmentation from oxazanickela(II)cyclobutanes

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Abstract

Reacting the low-valent nickel complex [(dtbpe)Ni]2(μ-η22-C6H6) with oxaziridines was found to form mixtures of imine, amide and aldehyde products. If the N-substituent of the oxaziridine is sufficiently bulky, a short-lived intermediate can be isolated and characterized by X-ray diffraction studies as an oxazanickela(II)cyclobutane. This is the first well-defined example of N–O oxidative addition of an oxaziridine to a transition metal. Subsequent fragmentation of this oxazanickelacyclobutane forms a complex mixture of products, including a nickel(II) imido complex, demonstrating that oxaziridines can serve as nitrene precursors. Preliminary mechanistic analysis is consistent with a bimetallic mechanism of fragmentation of the oxazanickelacyclobutane to form the nickel imido and η2-aldehyde complexes.

Graphical abstract: Oxaziridine cleavage with a low-valent nickel complex: competing C–O and C–N fragmentation from oxazanickela(ii)cyclobutanes

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Publication details

The article was received on 03 Oct 2017, accepted on 29 Oct 2017 and first published on 03 Nov 2017


Article type: Communication
DOI: 10.1039/C7CC07690H
Citation: Chem. Commun., 2017,53, 12442-12445
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    Oxaziridine cleavage with a low-valent nickel complex: competing C–O and C–N fragmentation from oxazanickela(II)cyclobutanes

    A. N. Desnoyer, W. Chiu, C. Cheung, B. O. Patrick and J. A. Love, Chem. Commun., 2017, 53, 12442
    DOI: 10.1039/C7CC07690H

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