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Bromine-lithium exchange on gem-dibromoalkenes part 1: batch vs microflow conditions

Abstract : The generation and reactivity of two model vinyl carbenoids from gem-dibromoalkenes 1 were studied in microflow systems. From substrate 1a (R = Ph, CF3), the lithium-bromine exchange could be simply performed within 30 ms at 20 °C with very good E-selectivity whereas the reaction was unselective under batch conditions, even at −78 °C. Moreover, the unstable carbenoid generated from 1b (R = Ph, H) could be trapped as the major product while only the Fritsch-Buttemberg-Wiechell rearrangement product was obtained in a flask under cryogenic conditions
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02899339
Contributor : Madeleine Roux-Merlin <>
Submitted on : Wednesday, July 15, 2020 - 9:46:12 AM
Last modification on : Thursday, July 16, 2020 - 3:40:58 AM

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  • HAL Id : hal-02899339, version 1

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Baptiste Picard, Katia Pérez, Thomas Lebleu, Daniela Vuluga, Fabrice Burel, et al.. Bromine-lithium exchange on gem-dibromoalkenes part 1: batch vs microflow conditions. Journal of flow chemistry, Akademiai Kiado, 2020, 10, pp.139-143. ⟨hal-02899339⟩

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