Rearrangement of Epoxynitriles: A Convenient Homologation of Acyclic and Cyclic Ketones to Carboxylic Acids
The Journal of Organic Chemistry2002Vol. 67(15), pp. 5440–5443
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Neil F. Badham, Wilford L. Mendelson, Andrew Allen, Ann M. Diederich, Drake S. Eggleston, John J. Filan, Alan J. Freyer, Lewis B. Killmer, Conrad J. Kowalski, Li Liu, Vance J. Novack, Frederick G. Vogt, Kevin S. Webb, Jennifer Yang
Abstract
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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