Stereoelectronic Effects on Dienophile Separation Influence the Diels-Alder Synthesis of Molecular Clefts

摘要

The formal cycloaddition adduct of 1,4-benzoquinone with two equivalents of cyclopentadiene is a scaffold with two non-conjugated alkenes. Both alkenes undergo endo [4+2] cycloaddition with a diene to form a rigid U-shaped molecular cleft. Here we show experimental, computational and structural evidence that π interactions between the alkenes affect structural rigidity, Diels-Alder reactivity, cleft formation and host- guest capture.