An Efficient Catalytic Method for the Beckmann Rearrangement of Ketoximes to Lactams by Cyanuric Chloride and Phosphazene Catalysts

Autor:	Yasutaka Ishii, Masaharu Hashimoto, Yasushi Obora
Rok vydání:	2009
Předmět:	chemistry.chemical_compound chemistry Laurolactam Organic Chemistry Cyanuric chloride Beckmann rearrangement Cyclohexanone oxime Trifluoroacetic acid Organic chemistry Physical and Theoretical Chemistry Oxime Toluene Phosphazene
Zdroj:	Organic Process Research & Development. 13:411-414
ISSN:	1520-586X 1083-6160
DOI:	10.1021/op800258s
Popis:	The Beckmann rearrangement of ketoximes to lactams was successfully achieved by a very small amount of cyanuric chloride and phosphazene by carrying out the reaction in a mixed solvent of trifluoroacetic acid and toluene under mild conditions. For instance, the Beckmann rearrangement of cyclohexanone oxime was completely performed under the influence of 0.5 mol % of cyanuric chloride (CNC) or phosphazene (1,3,5-triazo-2,4,6-triphosphorine-2,2,4,4,6,6-chloride: TAPC) in a 3:2 mixed solvent of trifluoroacetic acid and toluene at 70 °C for 4 h to give ϵ-caprolactam, which is an important monomer of 6-Nylon, in almost quantitative yield. The same strategy could be applied to laurolactam synthesis from cyclododecanone oxime.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::7a17a7931eaba7d1b11a9a580508210f https://doi.org/10.1021/op800258s Zobrazit plný text záznamu