Electron-Transfer Reduction of Butyryloxymethyloxirane with Alkalide K- , K+ (15-Crown-5)2

Author(s): Zbigniew Grobelny, Andrzej Stolarzewicz, Marcin Szczepanski, Adalbert Maercker.

Journal Name: Letters in Organic Chemistry

Volume 3 , Issue 7 , 2006

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Butyryloxymethyloxirane (glycidyl butyrate) is efficiently reduced with potassium anions of alkalide K-, K+(15-crown-5)2. The reaction proceeds via the corresponding radical anion, which decomposes the homolytic alkyl-oxygen bond cleavage or dimerizes. The oxirane ring is not opened by K-. No organometallic is formed as an intermediate. This shows that the mechanism of the process under study differs from that proposed earlier for alkyl glycidates. The position of the ester group in the substituent influences the behavior of the oxiranes.

Keywords: Butyryloxymethyloxirane, alkalide, potassium anion, radical anion, oxirane reduction

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Article Details

Year: 2006
Page: [564 - 566]
Pages: 3
DOI: 10.2174/157017806778341898
Price: $58