期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 67, 期 15, 页码 5440-5443出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo025737g
关键词
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A convenient two-step homologation of both aliphatic and aromatic ketones to the corresponding carboxylic acid has been developed. First ketones were converted to epoxynitriles with the Darzens reaction. Second, a Lewis acid mediated rearrangement of these epoxynitriles with lithium bromide was achieved to give homologated secondary alkanoic acids (as well as aryl-alkanoic) in good yields. The mechanism and the scope of the rearrangement reaction were investigated. This strategy constitutes a two-step homologation of ketones to secondary carboxylic acids.
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