Benzo[b]thiophene Fusion Enhances Local Borepin Aromaticity in Polycyclic Heteroaromatic Compounds was written by Messersmith, Reid E.;Yadav, Sangeeta;Siegler, Maxime A.;Ottosson, Henrik;Tovar, John D.. And the article was included in Journal of Organic Chemistry in 2017.Reference of 6287-82-7 This article mentions the following:
This report documents the synthesis, characterization, and computational evaluation of two isomeric borepin-containing polycyclic aromatics The syntheses of these two isomers involved sym. 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, crystallog., and computational characterization to literature compounds gave valuable insights about the aromaticity of these sym. 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 exptl. data demonstrate that the local borepin rings in these two compounds have a relatively high amount of aromatic character. Results from quantum chem. calculations provide a more comprehensive understanding of local and global aromatic characters of various rings in fused ring systems built upon boron heterocycles. In the experiment, the researchers used many compounds, for example, 2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7Reference of 6287-82-7).
2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7) belongs to benzothiophene derivatives. Benzothiophene finds use in research as a starting material for the synthesis of larger, usually bioactive structures. It is found within the chemical structures of pharmaceutical drugs such as raloxifene, zileuton, sertaconazole, and also BTCP.Reference of 6287-82-7
Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem