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Benzo[b]thiophene Fusion Enhances Local Borepin Aromaticity in Polycyclic Heteroaromatic Compounds
Johns Hopkins Univ, Dept Chem, 3400 North Charles St, Baltimore, MD 21218 USA..
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Molecular Biomimetics.
Johns Hopkins Univ, Dept Chem, 3400 North Charles St, Baltimore, MD 21218 USA..
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Molecular Biomimetics.
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2017 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 82, no 24, p. 13440-13448Article in journal (Refereed) Published
Abstract [en]

This report documents the synthesis, characterization, and computational evaluation of two isomeric borepin-containing polycyclic aromatics. The syntheses of these two isomers involved symmetrical disubstituted alkynes that were reduced to Z-olefins followed by borepin formation either through an isolable stannocycle intermediate or directly from the alkene via the trapping of a transient dilithio intermediate. Comparisons of their magnetic, crystallographic, and computational characterization to literature compounds gave valuable insights about the aromaticity of these symmetrically fused [b,f]borepins. The fusion of benzo[b]thiophene units to the central borepin cores forced a high degree of local aromaticity within the borepin moieties relative to other known borepin-based polycyclic aromatics. Each isomer had unique electronic responses in the presence of fluoride anions. The experimental data demonstrate that the local borepin rings in these two compounds have a relatively high amount of aromatic character. Results from quantum chemical calculations provide a more comprehensive understanding of local and global aromatic characters of various rings in fused ring systems built upon boron heterocycles.

Place, publisher, year, edition, pages
2017. Vol. 82, no 24, p. 13440-13448
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Organic Chemistry
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URN: urn:nbn:se:uu:diva-337849DOI: 10.1021/acs.joc.7b02512ISI: 000418392600048PubMedID: 29136463OAI: oai:DiVA.org:uu-337849DiVA, id: diva2:1170983
Available from: 2018-01-05 Created: 2018-01-05 Last updated: 2018-05-18Bibliographically approved

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Ottosson, Henrik

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