Chandrasekhar, Sosale and Gopalaiah, Kovuru (2001) Beckmann rearrangement in the solid state: reaction of oxime hydrochlorides. In: Tetrahedron Letters, 42 (45). pp. 8123-8125.
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Several ketoxime hydrochlorides undergo Beckmann rearrangement upon heating below their melting points for 5-48 h, in excellent yields (generally >70%). The absence of a reaction solvent and of by-products (except for HCl) makes for a very simple work-up. Aldoxime hydrochlorides apparently undergo dehydration to the corresponding nitriles under the above conditions. Dibenzyl ketoxime hydrochloride unexpectedly furnished a pyrazine derivative (67%), presumably via further reaction of the intermediate nitrilium ion in the crystal lattice.
|Item Type:||Journal Article|
|Additional Information:||Copyright of this article belongs to Elsevier.|
|Keywords:||Beckmann;nitrile ylide;oxime hydrochlorides;pyrazine;rearrangement;solid state.|
|Department/Centre:||Division of Chemical Sciences > Organic Chemistry|
|Date Deposited:||26 Sep 2008 04:47|
|Last Modified:||19 Sep 2010 04:50|
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