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Beckmann rearrangement in the solid state: reaction of oxime hydrochlorides

✍ Scribed by Sosale Chandrasekhar; Kovuru Gopalaiah

Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
51 KB
Volume
42
Category
Article
ISSN
0040-4039

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✦ Synopsis

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.

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