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Synthesis 2001(10): 1453-1455
DOI: 10.1055/s-2001-16089
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of α,β-Epoxy Ketones from Alkyl- and Arylsubstituted Cyclopropanols

Oleg G. Kulinkovich*, Dmitry A. Astashko, Vladimir I. Tyvorskii, Natalya A. Ilyina
Department of Chemistry, Belarussian State University, Fr. Skorina Av. 4, 220050 Minsk, Belarus
Fax: +375(0172)264998; e-Mail: kulinkovich@chem.bsu.unibel.by;
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Publication History

Received 31 January 2001
Publication Date:
23 September 2004 (online)

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Abstract

A number of aliphatic and arylaliphatic α,β-epoxy ketones were prepared in good yields in a one-pot procedure by a manganese-catalyzed ring cleavage of 1-substituted and 1,2-disubstituted cyclopropanols with oxygen followed by dehydration of the resulting cyclic peroxides with alkali.

Key words

epoxides - ketones - cyclopropanes - oxidations - transition metals

    References and Notes

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8

The rate of oxidation of cyclopropanols 1a-g on air was dramatically depressed, and so intensive bubbling with atmospheric O2 was required in this case to perform the reaction. The replacement of benzene by the non-flammable chlorinated C1-hydrocarbons led to the formation of halogen-containing compounds as by-products.