Journal
RUSSIAN CHEMICAL BULLETIN
Volume 54, Issue 4, Pages 1003-1007Publisher
SPRINGER
DOI: 10.1007/s11172-005-0348-7
Keywords
unsaturated carbonyl compounds; acetals; 1,3-dioxolanes; diazomethane; cyclopropanes; metal complex catalysis; cyclopropanation
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The present study concerned with the influence of the nature of the acetal fragment in unsaturated compounds on the reactivity of the C=C bond in cyclopropanation reactions with diazomethane catalyzed by copper and palladium compounds. The acetal substituents at the alpha- or gamma-position with respect to the C=C bond were found to exert an activating effect on the yields of cyclopropanation products compared to the starting unsaturated carbonyl compounds, which give 1,3-dipolar cycloaddition adducts with CH2N2 as by-products. Cyclopropanation of the double bonds appeared to be most efficiently catalyzed by Pd(acac)(2).
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