SCHEDULED MAINTENANCE
Oxaziridine cleavage with a low-valent nickel complex: competing C–O and C–N fragmentation from oxazanickela(ii)cyclobutanes†
Abstract
Reacting the low-valent nickel complex [(dtbpe)Ni]2(μ-η2:η2-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.
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