Planar [6]Radialenes: Structure, Synthesis, and Aromaticity of Benzotriselenophene and Benzotrithiophene

Planar, but non‐aromatic: The title [6]radialenes, which contain thiophene and selenophene units (see the ORTEP diagrams), can be prepared in a straightforward manner. X‐ray crystal structures and the results of theoretical studies show that the central six‐membered ring of these compounds, although...

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Published inAngewandte Chemie (International ed.) Vol. 46; no. 46; pp. 8814 - 8818
Main Authors Patra, Asit, Wijsboom, Yair H, Shimon, Linda J.W, Bendikov, Michael
Format Journal Article
LanguageEnglish
Published Weinheim Wiley-VCH Verlag 01.01.2007
WILEY-VCH Verlag
WILEY‐VCH Verlag
Wiley
Subjects
aromaticity
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
radialenes
Science & Technology
selenium
structural properties
sulfur heterocycles
COMPLEX
BENZENE
MOLECULAR-STRUCTURE
INDUCED BOND LOCALIZATION
CRYSTAL-STRUCTURE
sulfur heterocycles
NICS
structural properties
selenium
radialenes
DERIVATIVES
EXPANDED RADIALENES
aromaticity
INDEPENDENT CHEMICAL-SHIFTS
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Summary:Planar, but non‐aromatic: The title [6]radialenes, which contain thiophene and selenophene units (see the ORTEP diagrams), can be prepared in a straightforward manner. X‐ray crystal structures and the results of theoretical studies show that the central six‐membered ring of these compounds, although planar and composed entirely of sp2‐hybridized carbon atoms, is completely non‐aromatic.
Bibliography:http://dx.doi.org/10.1002/anie.200703123
ArticleID:ANIE200703123
MINERVA Foundation
istex:4581806D8CEEB5F86FBE9905228715B49B13F561
We thank Prof. Amnon Stanger (Technion) and Prof. D. F. Perepichka (McGill University) for helpful discussions. This research is supported by the MINERVA Foundation. M.B. is the incumbent of the Recanati Career Development Chair and a member ad personam of the Lise Meitner-Minerva Center for Computational Quantum Chemistry.
ark:/67375/WNG-Q1C2M65Z-9
We thank Prof. Amnon Stanger (Technion) and Prof. D. F. Perepichka (McGill University) for helpful discussions. This research is supported by the MINERVA Foundation. M.B. is the incumbent of the Recanati Career Development Chair and a member ad personam of the Lise Meitner‐Minerva Center for Computational Quantum Chemistry.
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200703123