Debromination of 1,2-Bis(phenylseleno)benzene Dibromide

Saito, Masaichi; Fujita, Masahiro; Kanatomi, Yoshihiko; Ishimura, Kazuya

doi:10.1246/bcsj.20130098

Cited by 2 publications

(1 citation statement)

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“…As judged from this MO feature in 1 , the dicationic species of 5 a and 5 c are also predicted to be stable due to similar characteristics found in the HOMOs of the model compounds 8 a and 8 d (Figure ). In the oxidation of 6 , the intermediary generated dicationic species would undergo a cyclization reaction to afford a selenanthrenium species, as was observed in the oxidation of 2 , because the cyclic delocalization in its HOMO is interrupted by the absence of heteroatoms.…”

Section: Figurementioning

confidence: 99%

Efficient Synthesis of 1,4‐Bis‐heteroatom‐substituted Tetraselanylbenzenes via 1,4‐Dilithiation of Hexaselanylbenzene and Investigation on Their Electronic Properties

Fujita

Furukawa

Saito

2017

Chemistry An Asian Journal

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We successfully synthesized mono- and bis-substituted polyselanylbenzenes 3 and 5 via mono- and dilithiation of hexakis(phenylselanyl)benzene (1), respectively. Introduction of various heteroatom functionalities into hexaselanylbenzene changed the electronic properties dependent on the σ-symmetric circular orbitals that were formed by the interactions between neighboring heteroatoms. In the cyclic voltammetry and theoretical studies on bis-heteroatom-substituted benzenes 5, the extent of the interactions in the circular orbitals with σ-symmetry affected the stability of the cationic species of 5. This study would give insight into the molecular design for new σ-delocalized systems and inspire the development of tuning electronic properties of benzene derivatives by σ-type orbital interactions derived from heteroatom functionalities.

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Section: Figurementioning

confidence: 99%