Regioselective Dimerization of Methylcyclopentadiene inside Cucurbit[7]uril.

ABSTRACT: The molecular confinement within rigid macrocyclic receptors can trigger catalytic activity and steer the selectivity of organic reactions. In this work, the dimerization of methylcyclopentadiene (MCPD) isomers in the presence of cucurbit[7]uril (CB7) was found to display, besides a large rate acceleration, a striking regioselectivity in aqueous solution at pH 3, different from the products predominating in the absence of the supramolecular catalyst. Among the different possible regioisomers and diastereomers, the endo-3,7-dimethyl-3a,4,7,7a-tetrahydro-1H-4,7-methanoindene adduct was selectively formed, which is otherwise found only as a minor product in the dimerization of neat MCPD or in commercial dimeric mixtures. This product originates from the reaction of the heteroternary complex o

SUBMITTER: Assaf KI 

PROVIDER: S-EPMC11855239 | biostudies-literature | 2025 Feb

REPOSITORIES: biostudies-literature