Divergent Rearrangements of Vinylcyclopropane into Skipped Diene and Cyclopentene: Mechanism, Scope, and Limitations

Delbrassinne, Arnaud;Richald, Maximilien;Janssens, Julien;Robiette, Raphaël
(2021) European Journal of Organic Chemistry — Vol. 2021, n° 20, p. 2862-2868 (2021)

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  • Delbrassinne, ArnaudUCLouvain
    Author
  • Richald, MaximilienUCLouvain
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  • Janssens, JulienUCLouvain
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  • Robiette, Raphaëlorcid-logoUCLouvain
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Abstract
Vinylcyclopropanes are versatile intermediates in organic synthesis which undergo various rearrangements. We report a new rearrangement of vinylcyclopropane into skipped diene. A detailed mechanistic study revealed that this transformation involves regioselective ring-opening of the cyclopropane ring followed by 1,2-migration of one of the cyclopropane substituent. Interestingly, our investigations showed that skipped diene is the kinetic product of the process but formation of a more stable cyclopentene is also accessible. The fundamental understanding of the processes involved enabled the development of divergent methodologies allowing to obtain cyclopentene or skipped diene from vinylcyclopropane in a selective and controlled manner.
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Delbrassinne, A., Richald, M., Janssens, J., & Robiette, R. (2021). Divergent Rearrangements of Vinylcyclopropane into Skipped Diene and Cyclopentene: Mechanism, Scope, and Limitations. European Journal of Organic Chemistry, 2021(20), 2862-2868. https://doi.org/10.1002/ejoc.202100430 (Original work published 2021)