Reactions of diazoalkanes with unsaturated compounds 15. Catalytic reactions of unsaturated carbonyl compounds and their derivatives with diazomethane |
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| Authors: | M D Khanova R M Sultanova S S Zlotskii V A Dokichev Yu V Tomilov |
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| Institution: | (1) Institute of Organic Chemistry, Ufa Research Center, Russian Academy of Sciences, 71 prosp. Oktyabrya, 450054 Ufa, Russian Federation;(2) N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation |
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| Abstract: | 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 α- or γ-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.
Dedicated to Corresponding Member of the Russian Academy of Sciences E. P. Serebryakov on the occasion of his 70th birthday.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 979–983, April, 2005. |
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| Keywords: | unsaturated carbonyl compounds acetals 1 3-dioxolanes diazomethane cyclopropanes metal complex catalysis cyclopropanation |
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