A Continuation of the Dehydrocoupling of Organoborohydrides to Form BN-Heterocycles
Faculty Mentor
Eric Abbey
Presentation Type
Poster
Start Date
May 2025
End Date
May 2025
Location
PUB NCR
Primary Discipline of Presentation
Chemistry and Biochemistry
Abstract
The potentially aromatic boron-nitrogen heterocycle, 4-phenyl-1,2,3,6-tetrahydro-1,2,3,6-diazadiborine, containing two carbon, two boron, and two nitrogen atoms, with potential R groups attached to the nitrogen atoms, has still not yet been successfully synthesized and isolated. Ideally, this target molecule can be produced using a one-pot synthesis under conditions that promote efficiency and prevent degradation. A styryl bis-borohydride is synthesized which then undergoes dehydrocoupling, forming B-N bonds and liberating H2 gas, in the presence of a dinitrogen compound that encourages aromaticity (such as hydrazine, pyridazine, or hydrazobenzene). Two synthetic routes have been attempted which remove a hydride and form a Lewis acidic borane compound. Complexation with the dinitrogen compound is then attempted to afford the desired heterocycle. Results from the 11B NMR data suggest that certain dinitrogen compounds react more favorably than others, with pyridazine providing the most promising results. Although NMR indicates that the BN heterocycle may have formed, isolation of this compound is an ongoing challenge. Going forward, variations in the procedure can be made to assist in synthesis and isolation.
Recommended Citation
Mann, Kenzington Lee and Abbey, Eric, "A Continuation of the Dehydrocoupling of Organoborohydrides to Form BN-Heterocycles" (2025). 2025 Symposium. 39.
https://dc.ewu.edu/srcw_2025/ps_2025/p2_2025/39
Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-No Derivative Works 4.0 International License.
A Continuation of the Dehydrocoupling of Organoborohydrides to Form BN-Heterocycles
PUB NCR
The potentially aromatic boron-nitrogen heterocycle, 4-phenyl-1,2,3,6-tetrahydro-1,2,3,6-diazadiborine, containing two carbon, two boron, and two nitrogen atoms, with potential R groups attached to the nitrogen atoms, has still not yet been successfully synthesized and isolated. Ideally, this target molecule can be produced using a one-pot synthesis under conditions that promote efficiency and prevent degradation. A styryl bis-borohydride is synthesized which then undergoes dehydrocoupling, forming B-N bonds and liberating H2 gas, in the presence of a dinitrogen compound that encourages aromaticity (such as hydrazine, pyridazine, or hydrazobenzene). Two synthetic routes have been attempted which remove a hydride and form a Lewis acidic borane compound. Complexation with the dinitrogen compound is then attempted to afford the desired heterocycle. Results from the 11B NMR data suggest that certain dinitrogen compounds react more favorably than others, with pyridazine providing the most promising results. Although NMR indicates that the BN heterocycle may have formed, isolation of this compound is an ongoing challenge. Going forward, variations in the procedure can be made to assist in synthesis and isolation.
