Online Encyclopedia

OXIMES

Online Encyclopedia
Originally appearing in Volume V20, Page 419 of the 1911 Encyclopedia Britannica.
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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 : NOH—4R 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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