Cavitands endowed with in‐ and outwardly directed allylsilanes are described; epoxidation reactions of the allyl groups with meta‐chloroperbenzoic acid are included. The synthesis of introverted and extroverted allylsilanes tethered to triquinoxaline‐spanned resorcinarenes was successfully achieved. Competitive epoxidation experiments between the two isomers disclosed that the introverted allyl was more reactive than the extroverted allyl, despite a clearly congested nuisance: the vase‐formed cavity would actively stabilize the reaction process.
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