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Synthesis 1990; 1990(9): 787-789
DOI: 10.1055/s-1990-27016
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One-Pot Preparation of 1-Acyl-1-methoxycarbonyloxiranes and 1-Acyl-1-cyanooxiranes from Methyl 3-Hydroxy-2-methylenealkanoates or 3-Aryl-3-hydroxy-2-methylenepropanenitriles

André Foucaud* , Eliane le Rouillé
  • *Groupe de Chimie structurale associé au C.N.R.S., Université de Rennes, Campus de Beaulieu, F-35042 Rennes, France
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Publication Date:
17 September 2002 (online)

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The reaction of sodium hypochlorite with methyl 3-hydroxy-2methylenealkanoates or 3-aryl-3-hydroxy-2-methylenepropanenitriles, dispersed on silica gel, in acetonitrile leads to oxidation of the alcohol function and epoxidation of the methylene group to give 2,2-disubstituted oxiranes in good yield.

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