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Updated: Jul 31, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Bisazapentalene Dication: Global Aromaticity and Open-Shell Singlet Ground State
Yi Han1, Jun Zhu1, Shaoqiang Dong2
1Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore.
Abstract:
Antiaromatic moieties fused in polycyclic π-conjugated molecules usually exhibit strong localized antiaromaticiy. Herein, we reported the synthesis and properties of a bisazapentalene dication (BAP) obtained from in situ two-electron oxidation of neutral species 8. Noteworthily, it possesses global aromaticity and an open-shell singlet ground state. This study underlines the importance of heteroatoms in determining the delocalization of π-electrons and the aromaticity of molecules in their oxidized states.
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