Benzo[b]thiophene Fusion Enhances Local Borepin Aromaticity in Polycyclic Heteroaromatic Compounds

Messersmith, Reid E.Johns Hopkins Univ, Dept Chem, 3400 North Charles St, Baltimore, MD 21218 USA. (author)

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.

Yadav, SangeetaUppsala universitet,Molekylär biomimetik(Swepub:uu)sanya730 (author)
Siegler, Maxime A.Johns Hopkins Univ, Dept Chem, 3400 North Charles St, Baltimore, MD 21218 USA. (author)
Ottosson, HenrikUppsala universitet,Molekylär biomimetik(Swepub:uu)heott255 (author)
Tovar, John D.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. (author)
Johns Hopkins Univ, Dept Chem, 3400 North Charles St, Baltimore, MD 21218 USA.Molekylär biomimetik (creator_code:org_t)

In:Journal of Organic Chemistry: American Chemical Society (ACS)82:24, s. 13440-134480022-32631520-6904

By the author/editor: Messersmith, Rei ...; Yadav, Sangeeta; Siegler, Maxime ...; Ottosson, Henrik; Tovar, John D.

About the subject

NATURAL SCIENCES: NATURAL SCIENCES; and Chemical Science ...; and Organic Chemistr ...

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