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Synthesis 1999; 1999(4): 559-561
DOI: 10.1055/s-1999-3433
short paper
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Selective Conversion of Enol Ethers into Alcohols in the Presence of Alkenes Using Hg(OAc)2-NaBH4

R. David Crouch* , John F. Mehlmann, Brian R. Herb, Jeffrey V. Mitten, H. George Dai
  • *Department of Chemistry, Dickinson College, Box 1773, Carlisle, PA 17013-2896, USA; Fax +1(7 17)2 45 19 95; E-mail: crouch@dickinson.edu
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Publication Date:
31 December 1999 (online)

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Alkyl enol ethers derived from aldehydes undergo selective oxymercuration-demercuration with aqueous Hg(OAc)2-NaBH4 in the presence of an alkene in good to excellent yield. This method allows the survival of mono-, trans and cis di-, and tri-substituted alkenes as well as cyclic alkenes.

alcohols - alkenes - enol ethers - hydrolysis - reduction