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

Autor:	Arnaud Delbrassinne, Maximilien Richald, Julien Janssens, Raphaël Robiette
Přispěvatelé:	UCL - SST/IMCN/MOST - Molecular Chemistry, Materials and Catalysis
Rok vydání:	2021
Předmět:	cyclopentenes Scope (project management) Diene Chemistry rearrangement Organic Chemistry skipped dienes vinylcyclopropanes chemistry.chemical_compound Computational chemistry density functional calculations Cyclopentene Physical and Theoretical Chemistry Mechanism (sociology)
Zdroj:	European Journal of Organic Chemistry, Vol. 2021, no.20, p. 2862-2868 (2021)
ISSN:	1099-0690 1434-193X
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::1d53e726bc296bc70861c9aeb81ce238 https://doi.org/10.1002/ejoc.202100430 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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