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Encyclopedia Britannica



OXIMES

This article appears in Volume V20, Page 419 of the Encyclopedia Britannica.

Encyclopedia Britannica - Main :: ORC-PAI
OXIMES , in organic
chemistry
 , compounds containing the grouping > C : N OH, derived from aldehydes and ketones by condensing them with
hydroxylamine
 . Those derived from aldehydes are known as aldoximes, those from ketones as ketoximes. They were first prepared by V.
Meyer
  in 1882
(Bey., 1882, 15, pp. 1324, 1525, 2778). They are either colour-less liquids, which boil without decomposition, or crystalline solids; and are both basic and acidic in
character
 . On reduction by sodium amalgam in glacial acetic acid solution they yield
primary
  amines. They are hydrolysed by dilute
mineral
  acids
yielding
hydroxylamine
  and the
parent
  aldehyde or ketone.
The aldoximes are converted by the action of dehydrating
agents into nitriles: RCH : NOH4R C : N+H2O. The ket-
oximes by the action of acetyl chloride undergo a
peculiar
  intra-
molecular re-arrangement known as the
Beckmann
  trans-
formation (E.
Beckmann
 , Ber., 1886, 19, p. 989; 1887, 20, p.
2580), yielding as final products an acid-amide or anilide, thus:


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