Synthesis of O - and N -substituted pentaiodobenzenes bearing σ-symmetric delocalized orbitals using site-selective nucleophilic aromatic substitution reactions

We report the synthesis of oxygen- and nitrogen-substituted (O- and N-substituted) pentaiodobenzenes using site-selective nucleophilic aromatic substitution (SNAr) reactions. Single-crystal X-ray diffraction analysis and theoretical calculations of thus synthesized pentaiodobenzenes reveal that thei...

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Bibliographic Details
Published in:Chemistry letters 2024-02, Vol.53 (2)
Main Authors: Takada, Yuki, Minoura, Mao, Furukawa, Shunsuke, Saito, Masaichi
Format: Article
Language:English
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Summary:We report the synthesis of oxygen- and nitrogen-substituted (O- and N-substituted) pentaiodobenzenes using site-selective nucleophilic aromatic substitution (SNAr) reactions. Single-crystal X-ray diffraction analysis and theoretical calculations of thus synthesized pentaiodobenzenes reveal that their highest occupied molecular orbital (HOMOs) are composed of circularly delocalized σ-symmetric orbitals, as found in hexa-substituted benzenes bearing heavy atoms such as selenium and iodine.
ISSN:0366-7022
1348-0715
DOI:10.1093/chemle/upad040