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 degrees C.

Automated summary

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.