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Benzo[b]thiophene F...
Benzo[b]thiophene Fusion Enhances Local Borepin Aromaticity in Polycyclic Heteroaromatic Compounds
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- Messersmith, Reid E. (författare)
- Johns Hopkins Univ, Dept Chem, 3400 North Charles St, Baltimore, MD 21218 USA.
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- Yadav, Sangeeta (författare)
- Uppsala universitet,Molekylär biomimetik
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- Siegler, Maxime A. (författare)
- Johns Hopkins Univ, Dept Chem, 3400 North Charles St, Baltimore, MD 21218 USA.
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- Ottosson, Henrik (författare)
- Uppsala universitet,Molekylär biomimetik
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- Tovar, John D. (författare)
- Johns Hopkins Univ, Dept Chem, 3400 North Charles St, Baltimore, MD 21218 USA.;Johns Hopkins Univ, Dept Mat Sci & Engn, 3400 North Charles St, Baltimore, MD 21218 USA.
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Johns Hopkins Univ, Dept Chem, 3400 North Charles St, Baltimore, MD 21218 USA Molekylär biomimetik (creator_code:org_t)
- 2017-11-28
- 2017
- Engelska.
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Ingår i: Journal of Organic Chemistry. - : American Chemical Society (ACS). - 0022-3263 .- 1520-6904. ; 82:24, s. 13440-13448
- Relaterad länk:
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https://urn.kb.se/re...
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https://doi.org/10.1...
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Abstract
Ämnesord
Stäng
- 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.
Ämnesord
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
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