The supramolecular hydrogen-bonded self-assembled resorcinarene hexameric capsule promotes the ring closing isomerization of cannabidiol through encapsulation of the intermediate carbocation species formed by protonation with HCl. The confinement effect imparted by the capsule steers product selectivity towards the uncommon products Delta 8-iso-THC, Delta 4(8)-iso-THC, together with the hydrated 8-Hydroxy-iso-THC.The confinement effect provided by the resorcinarene hydrogen bonded capsule in the presence of HCl accelerates the isomerization of cannabidiol leading to cyclic and hydrated products that are uncommon compared to the same reaction with traditional strong Bronsted acids, thus widening the chemical scenario provided by the capsule. image
Confinement Effects in Catalysis: Steering the Product Selectivity in Cannabidiol Isomerization by the Resorcinarene Supramolecular Capsule
Bordignon, Francesca;Calmanti, Roberto;Perosa, Alvise;Fabris, Fabrizio;Scarso, Alessandro
2024-01-01
Abstract
The supramolecular hydrogen-bonded self-assembled resorcinarene hexameric capsule promotes the ring closing isomerization of cannabidiol through encapsulation of the intermediate carbocation species formed by protonation with HCl. The confinement effect imparted by the capsule steers product selectivity towards the uncommon products Delta 8-iso-THC, Delta 4(8)-iso-THC, together with the hydrated 8-Hydroxy-iso-THC.The confinement effect provided by the resorcinarene hydrogen bonded capsule in the presence of HCl accelerates the isomerization of cannabidiol leading to cyclic and hydrated products that are uncommon compared to the same reaction with traditional strong Bronsted acids, thus widening the chemical scenario provided by the capsule. image
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