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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Abstract

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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