ArticleThe Journal of organic chemistry2025
An Unusual Friedel-Crafts Reaction and Violation of the Markovnikov Rule in the Formation of an Adamantyl Arene.
Article in The Journal of organic chemistry, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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Abstract
Yoshihara, Hiroki, Yagi, and Itami utilized an unusual Friedel-Crafts-like alkylation in the synthesis of an adamantane-annulated arene. The precursor was a 3° carbocation, which they proposed undergoes a Wagner-Meerwein shift to a 2° carbocation, which subsequently alkylates a benzene ring. This mechanism was supported by their DFT calculations. However, their choice of the B3LYP functional often finds false transition structures. A more appropriate functional showed that the alkylation occurs via a concerted reaction.
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