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Updated: Sep 19, 2025

Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
Rethinking aromaticity of reduced thienoquinoids: insights from an S-Pechmann dye dianion
Takumi Shiokawa1, Aiko Fukazawa2
1Department of Energy and Hydrocarbon, Graduate School of Engineering, Kyoto University, Japan.
Abstract:
A dianionic species of a thienoquinoid derivative bearing a cross-conjugated γ-thiolactone, the so-called S-Pechmann dye, has been synthesized and characterized. Comparative analysis with a pentafulvalene dianion with an isoelectronic structure revealed that the S-Pechmann dye dianion exhibits significantly reduced aromatic character due to preferential charge delocalization over the C4O units. This work provides an in-depth understanding of the fundamental electronic nature of thienoquinoid-based compounds.
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