Electrophilic Substitution of Asymmetrically Distorted Benzenes within Triptycene Derivatives
Keisuke Ueno1, Yuji Nishii1, Masahiro Miura1
1Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan.
Abstract:
Herein, we disclose a unique directing effect of 9-substituted triptycenes in electrophilic substitution to achieve the regioselective functionalization of the triptycene core. The Hirshfeld population analysis was adopted to predict the selectivity in electrophilic substitution. TMS and t-Bu groups were found to considerably accelerate the reaction at C2 positions to produce C3-symmetric isomers. Correlation between distortion and charge distribution within benzene rings was systematically examined.
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