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Rearrangement of epoxynitriles: a convenient homologation of acyclic and cyclic ketones to carboxylic acids.

Authors
  • Badham, Neil F
  • Mendelson, Wilford L
  • Allen, Andrew
  • Diederich, Ann M
  • Eggleston, Drake S
  • Filan, John J
  • Freyer, Alan J
  • Killmer, Lewis B Jr
  • Kowalski, Conrad J
  • Liu, Li
  • Novack, Vance J
  • Vogt, Frederick G
  • Webb, Kevin S
  • Yang, Jennifer
Type
Published Article
Journal
The Journal of organic chemistry
Publication Date
Jul 26, 2002
Volume
67
Issue
15
Pages
5440–5443
Identifiers
PMID: 12126449
Source
Medline
License
Unknown

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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