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| - Competition between Alkenes in Intramolecular Ketene−Alkene[2 + 2] Cycloaddition: What Does It Take to Win?
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| - In the course of developing a new synthetic methodology using ketenes in sequential cycloadditionsteps, we were faced with a competition problem with molecules containing a ketene tethered tomore than one reacting partner. To pinpoint the electronic and tethering requirements for achemoselective reaction, we undertook a series of ketene−alkene [2 + 2] cycloaddition competitionexperiments. Those experiments were conducted on molecules containing either two identical alkeneshaving different tether lengths or two alkenes having the same tether length but being electronicallydifferent. We demonstrated that the reaction is much faster for forming five-membered rings thansix-membered rings and calculated the Hammett constant ρ for intramolecular ketene−alkene[2 + 2] cycloadditions to be −1.39.
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