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Synthesis of α,β-Unsaturated Aldehydes with an (E)-Trisubstituted Double Bond via Ring Opening of Cyclopropanols

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Abstract

An efficient method has been developed for the first time for the synthesis of α,β-unsaturated aldehydes with an (E)-trisubstituted C=C double bond by oxidation of mixtures of regio- and stereoisomeric allyl bromides without their preliminary separation. The substrates are available via ring opening of 1,2-disub­stituted cyclopropyl sulfonates. Allyl bromides containing additional functional groups were oxidized with N-methylmorpholine N-oxide more effectively. The reactions were carried out in solvents favoring nucleophilic substitution, and elevated temperature and prolonged reaction increased the fraction of the E isomer and reduced the amount of isomeric ketone.

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Authors and Affiliations

  1. Belarusian State University, 220047, Minsk, Belarus

    V. S. Masyuk, Yu. Yu. Kozyrkov & I. V. Mineeva

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  1. V. S. Masyuk
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  2. Yu. Yu. Kozyrkov
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  3. I. V. Mineeva
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Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 10, pp. 1357–1370 https://doi.org/10.31857/S0514749221100013.

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Masyuk, V.S., Kozyrkov, Y.Y. & Mineeva, I.V. Synthesis of α,β-Unsaturated Aldehydes with an (E)-Trisubstituted Double Bond via Ring Opening of Cyclopropanols. Russ J Org Chem 57, 1563–1574 (2021). https://doi.org/10.1134/S1070428021100018

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