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.
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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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Khanova, M.D., Sultanova, R.M., Zlotskii, S.S. et al. Reactions of diazoalkanes with unsaturated compounds 15. Catalytic reactions of unsaturated carbonyl compounds and their derivatives with diazomethane. Russ Chem Bull 54, 1003–1007 (2005). https://doi.org/10.1007/s11172-005-0348-7
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DOI: https://doi.org/10.1007/s11172-005-0348-7