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Preparation of Amines: Reduction of Oximes and Nitro Compounds

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Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
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Reduction of Nitrogen Oxides by Dimagnesium(I) Compounds.

Jeremy C Mullins¹, Matthew J Evans¹, Joseph M Parr¹

¹School of Chemistry, PO Box 23, Monash University, Clayton, VIC 3800, Australia.

Inorganic Chemistry

|January 14, 2026

Summary

Dimagnesium(I) reagents react with nitrous oxide and nitroxyl radicals to form novel magnesium complexes. These reactions showcase new pathways for magnesium chemistry and the synthesis of unique oxide and nitroxyl species.

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Area of Science:

Organometallic Chemistry
Main Group Chemistry
Inorganic Synthesis

Background:

Low-valent magnesium compounds are reactive intermediates.
Nitrous oxide (N2O) and nitroxyl radicals (NHC-NO•) are versatile reagents.
Understanding the reactivity of low-valent magnesium is crucial for developing new synthetic methodologies.

Purpose of the Study:

To explore the reactivity of dimagnesium(I) reagents with N2O and NHC-NO• radicals.
To synthesize and characterize novel magnesium complexes containing oxide and nitroxyl moieties.
To investigate the electronic structure and reaction mechanisms of these new complexes.

Main Methods:

Synthesis of dimagnesium(I) reagents and their reactions with N2O and NHC-NO•.
Isolation and characterization of products using X-ray crystallography and NMR spectroscopy.
Computational studies (DFT) to elucidate electronic structures and reaction pathways.

Main Results:

Formation of a tetra-magnesium oxide/hyponitrite complex [{(NCN^Dipp)Mg}(μ-N₂O₂){Mg(NCN^Dipp)}₂(μ-O){Mg(NCN^Dipp)}] (1) from dimagnesium(I) and N2O.
Synthesis of NHC-nitroxyl complexes [(NCN^Dipp)Mg(κ²-N,O-ON-NHC^Dipp)] (2) and [(BDI^Dipp)Mg(κ²-N,O-ON-NHC^Mes)] (3) via reduction of NHC-NO• radicals by dimagnesium(I) reagents.
Reaction of a magnesium(II) butyl complex with NHC^Dipp-NO• yielding [(BDI^Dipp)Mg(κ¹-O-ON-NHC^Dipp)(THF)] (4) and n-octane.

Conclusions:

Dimagnesium(I) reagents exhibit rich reactivity towards N2O and nitroxyl radicals, enabling the formation of unique magnesium complexes.
The study demonstrates novel synthetic routes to magnesium-containing oxide, hyponitrite, and nitroxyl species.
Computational and experimental data provide insights into the electronic structure and reaction mechanisms involving low-valent magnesium.