期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 87, 期 16, 页码 11141-11147出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c01394
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资金
- French Ministe`re de l'Enseignement Superieur et de la Recherche (MESR)
- Aix-Marseille Universite (AMU)
- Centre National de la Recherche Scientifique (CNRS)
- Centrale Marseille
By combining theoretical calculations and experimental measurements, the kinetic constant of the cycloaddition reaction between a specially designed nonracemic aryne atropisomer and furan in solution was determined. The reaction half-life of this aryne atropisomer with 100 equivalents of furan as the trapping reagent was found to be <150 ns at temperatures above -20 degrees C.
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 degrees C.
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