Atom Swapping Reaction on Diborylcarbenoid: Synthesis and Electronic Structure of Inorganic Chalcogenophene Analogues
- 1Department of Chemistry and Biotechnology Graduate School of Engineering The University of Tokyo Bunkyo‐ku Tokyo Japan
- 2Department of Chemistry Graduate School of Science Tokyo Metropolitan University Hachioji Tokyo Japan
Abstract
Inorganic analogues of aromatic compounds, wherein C═C bonds are replaced with B─N bonds, are isoelectronic with the original aromatic compounds, however, they can show different properties. While borazine, an inorganic analogue of benzene, has been well‐studied, inorganic analogues of chalcogenophene have been less explored. Here, we synthesized crystalline isolable inorganic furan 2O and thiophene 2S by atom swapping reaction at the carbenoid carbon of K/Cl‐diborylcarbenoid, an equivalent to diborylcarbene. Density functional theory calculation exhibited that, in contrast to the quite weak aromatic character of borazine, inorganic chalcogenophenes 2O and 2S have a moderate aromaticity. Theoretical investigation of the reaction mechanism suggested that the atom swapping reaction occurred via oxidation of diborylcarbenoid 1 to diboralactone intermediate 3Ch and the following intramolecular rearrangement reaction.
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BibTeX
@article{shibutani2026atom,
title = {{Atom Swapping Reaction on Diborylcarbenoid: Synthesis and Electronic Structure of Inorganic Chalcogenophene Analogues}},
author = {Yuki Shibutani and Momoko Inaoka and Shuhei Kusumoto and Kyoko Nozaki},
journal = {Chemistry (Weinheim an Der Bergstrasse, Germany)},
year = {2026},
month = jul,
doi = {10.1002/chem.202500433},
url = {https://doi.org/10.1002/chem.202500433},
note = {CC BY 4.0},
}
RIS
TY - JOUR
TI - Atom Swapping Reaction on Diborylcarbenoid: Synthesis and Electronic Structure of Inorganic Chalcogenophene Analogues
AU - Yuki Shibutani
AU - Momoko Inaoka
AU - Shuhei Kusumoto
AU - Kyoko Nozaki
PY - 2026
DA - 2026/07/17
JO - Chemistry (Weinheim an Der Bergstrasse, Germany)
DO - 10.1002/chem.202500433
UR - https://doi.org/10.1002/chem.202500433
AB - Inorganic analogues of aromatic compounds, wherein C═C bonds are replaced with B─N bonds, are isoelectronic with the original aromatic compounds, however, they can show different properties. While borazine, an inorganic analogue of benzene, has been well‐studied, inorganic analogues of chalcogenophene have been less explored. Here, we synthesized crystalline isolable inorganic furan 2O and thiophene 2S by atom swapping reaction at the carbenoid carbon of K/Cl‐diborylcarbenoid, an equivalent to diborylcarbene. Density functional theory calculation exhibited that, in contrast to the quite weak aromatic character of borazine, inorganic chalcogenophenes 2O and 2S have a moderate aromaticity. Theoretical investigation of the reaction mechanism suggested that the atom swapping reaction occurred via oxidation of diborylcarbenoid 1 to diboralactone intermediate 3Ch and the following intramolecular rearrangement reaction.
SN - 0947-6539
SN - 1521-3765
ER -