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Korean Chemical Society (대한화학회)
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Selective Reduction of Oximes to N-Monosubstituted Hydroxylamines with Lithium Borohydride

  • Published : 1988.10.20
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Abstract

Selective reduction of aldoximes and ketoximes with lithium borohydride in tetrahydrofuran was investigated. Thus, aldoximes and cyclic ketoximes such as hexanaldoxime, heptanaldoxime, cyclopentanone oxime and cyclohexanone oxime were reduced smoothly to the corresponding N-monosubstituted hydroxylamines at room temperature in 65-93% yield. The reduction of alicyclic ketoxime was very slow, requiring somewhat high reaction temperature ($65^{\circ}C$) for the complete reduction to give the hydroxnylamines. The reduction of aromatic oximes such as benzaldoxime and acetophenone oxime was very sluggish, giving a mixture of the corresponding hydroxylamines and amines at $65^{\circ}C$.

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References

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  1. ChemInform Abstract: Selective Reduction of Oximes to N‐Monosubstituted Hydroxylamines with Lithium Borohydride. vol.20, pp.16, 1988, https://doi.org/10.1002/chin.198916111
  2. A Rapid and Practical Protocol for Solvent-Free Reduction of Oximes to Amines with NaBH4/ZrCl4/Al2O3 System vol.32, pp.9, 1988, https://doi.org/10.5012/bkcs.2011.32.9.3448