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Synlett 1992; 1992(7): 587-588
DOI: 10.1055/s-1992-21425
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Intramolecular Homolytic Displacements; Part 21: An Easy Access to α,β-Epoxy Esters through the Homolytic Induced Decomposition of Alkyl 2-(1-tert-Butylperoxyalkyl)propenoates

Charles Navarro* , Marie Degueil-Castaing, Daniel Colombani, Bernard Maillard
  • *Laboratoire de Chimie Organique et Organométallique, associé au CNRS (URA 35), Université Bordeaux 1, F-33405 Talence Cedex, France
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Publikationsdatum:
08. März 2002 (online)

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The induced decomposition of alkyl 2-(1-tert-butylperoxyalkyl) propenoates was identified as an easy way of preparing α,β-epoxy esters. For example, ethyl 2-tert-butylperoxymethylpropenoate (1) and toluene underwent a radical reaction initiated by the homolysis of tert-butyl peracetate to form 1-ethoxycarbonyl-1-phenethyloxirane (11) in 60% yield.

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