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Allylic oxidation: easy synthesis of alkenones from activated alkenes with TEMPO

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
46
Issue
14
Identifiers
DOI: 10.1016/j.tetlet.2005.02.032
Keywords
  • Oxidation
  • Tempo
  • Electrosynthesis
Disciplines
  • Chemistry

Abstract

Abstract Activated alkenes and dienes are converted into the corresponding alkenone in excellent yields (>90%). In aqueous acetonitrile, the transformations are catalyzed by 2,2,6,6-tetramethyl-1-oxopiperidinium (TEMPO +) in the presence of water and 2,6-lutidine. TEMPO + cations were regenerated electrochemically from the radical parent (TEMPO ) at a vitreous carbon anode.

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