Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Non-Electronic Aromatic Ring Activation by Simple Steric Repulsion between Substituents in 1-Methylquinolinium Salt Systems
Kento IwaiSoichi YokoyamaHaruyasu AsaharaNagatoshi Nishiwaki
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2020 Volume 93 Issue 1 Pages 50-57


A systematic study of non-electronic activation of an aromatic ring was performed using a series of 8-substituted 1-methylquinolinium salts. As the 8-substituent became bulkier, the quinoline framework was distorted by steric repulsion between substituents at the 1- and 8-positions. This was accompanied by lack of coplanarity, which brought about dearomatization. Consequently, quinolinium ions possessing a bulky 8-substituent exhibited high reactivity undergoing nucleophilic addition at the 2-position efficiently. We demonstrate that the activation was achieved sterically and not electronically.

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