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

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.

epoxides - ketones - cyclopropanes - oxidations - transition metals

References and Notes

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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.

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