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

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.

Citation

Guillaume Dauvergne, Nicolas Vanthuyne, Michel Giorgi, Jean Rodriguez, Yannick Carissan, Yoann Coquerel. Determination of the Rate Constant of the [4 + 2] Cycloaddition Between an Aryne Atropisomer and Furan in Solution. The Journal of organic chemistry. 2022 Aug 19;87(16):11141-11147

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PMID: 35946800

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