An Unusual Friedel–Crafts Reaction and Violation of the Markovnikov Rule in the Formation of an Adamantyl Arene DOI Creative Commons
B. Andes Hess, Lidia Smentek

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 14, 2025

Yoshihara, Hiroki, Yagi, and Itami utilized an unusual Friedel-Crafts-like alkylation in the synthesis of adamantane-annulated arene. The precursor was a 3° carbocation, which they proposed undergoes Wagner-Meerwein shift to 2° subsequently alkylates benzene ring. This mechanism supported by their DFT calculations. However, choice B3LYP functional often finds false transition structures. A more appropriate showed that occurs via concerted reaction.

Language: Английский

An Unusual Friedel–Crafts Reaction and Violation of the Markovnikov Rule in the Formation of an Adamantyl Arene DOI Creative Commons
B. Andes Hess, Lidia Smentek

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 14, 2025

Yoshihara, Hiroki, Yagi, and Itami utilized an unusual Friedel-Crafts-like alkylation in the synthesis of adamantane-annulated arene. The precursor was a 3° carbocation, which they proposed undergoes Wagner-Meerwein shift to 2° subsequently alkylates benzene ring. This mechanism supported by their DFT calculations. However, choice B3LYP functional often finds false transition structures. A more appropriate showed that occurs via concerted reaction.

Language: Английский

Citations

0