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Beckmann rearrangement in the solid state: reaction of oxime hydrochlorides

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
Publication: Tetrahedron Letters
Publisher: Elsevier
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
URI: http://eprints.iisc.ac.in/id/eprint/16039

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