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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 9, Number 5
May 20, 1988 

Selective Reduction of Oximes to N-Monosubstituted Hydroxylamines with Lithium Borohydride
Byung Tae Cho*, See Yearl Seong
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℃) 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℃.
322 - 324
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