Rearrangement of epoxynitriles: a convenient homologation of acyclic and cyclic ketones to carboxylic acids.
- Published Article
The Journal of organic chemistry
- Publication Date
Jul 26, 2002
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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The corresponding record at NLM can be accessed at https://www.ncbi.nlm.nih.gov/pubmed/12126449