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Cyanuric chloride as a mild and active Beckmann rearrangement catalyst.

Journal of the American Chemical Society (2005-08-11)
Yoshiro Furuya, Kazuaki Ishihara, Hisashi Yamamoto
ABSTRACT

The first general organocatalytic Beckmann rearrangement of ketoximes into amides has been realized by the catalytic use of cyanuric chloride. Furthermore, acids such as HCl and ZnCl2 are effective as cocatalysts with cyanuric chloride. For example, azacyclotridecan-2-one, which is synthetically useful as a starting material for nylon-12, was prepared in quantitative yield by the Beckmann rearrangement of cyclododecanone oxime (100 mmol scale) catalyzed by cyanuric chloride (0.5 mol %) and ZnCl2 (1 mol %).

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Cyanuric chloride, 99%