Determination of the Rate Constant of the [4 + 2] Cycloaddition Between an Aryne Atropisomer and Furan in Solution - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Journal of Organic Chemistry Année : 2022

Determination of the Rate Constant of the [4 + 2] Cycloaddition Between an Aryne Atropisomer and Furan in Solution

Résumé

Using a specially designed prototype of a nonracemic aryne atropisomer with a low barrier to enantiomerization (ca. 36 kJ•mol −1), it was possible to determine the kinetic constant of its cycloaddition with furan in solution by a combination of theoretical calculations and experimental measurements. It was found that the reaction half-life of this aryne atropisomer in solution with 100 equivalents of furan as the trapping reagent is <150 ns at temperatures above −20 °C. pubs.acs.org/joc Article

Domaines

Chimie organique
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Dates et versions

hal-03777717 , version 1 (15-09-2022)

Identifiants

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Guillaume Dauvergne, Nicolas Vanthuyne, Michel Giorgi, Jean Rodriguez, Yannick Carissan, et al.. Determination of the Rate Constant of the [4 + 2] Cycloaddition Between an Aryne Atropisomer and Furan in Solution. Journal of Organic Chemistry, 2022, 87 (16), pp.11141-11147. ⟨10.1021/acs.joc.2c01394⟩. ⟨hal-03777717⟩

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