Dehydro Coupling of Organoborohydrides to Form BN-Heterocycles
Faculty Mentor
Dr. Eric Abbey
Presentation Type
Poster
Start Date
5-8-2024 9:00 AM
End Date
5-8-2024 10:45 AM
Location
PUB NCR
Primary Discipline of Presentation
Chemistry and Biochemistry
Abstract
Currently, there has not been a way to synthesize the potentially aromatic nitrogen-boron heterocycle (4-phenyl-1,2,3,6-tetrahydro-1,2,3,6-diazadiborine), which contains two carbons, two borons, and two nitrogen atoms. The goal of this project is to create a synthetic pathway that can be done in a “one-pot” synthesis as well as in a suitable environment to prevent the compound from degrading. There have been two procedures we have been following in efforts to produce our compound. The first procedure reacts styryl bis(BPin) with either LiAlH4 or NaAlH4 to create a styryl borohydride followed by adding hydrazine dihydrochloride. The second procedure uses styryl bis(BF3K) as the starting material rather than styryl bis(BPin) and follows the same additions. This reaction is a dehydro coupling, forming B-N bonds. The results from these reactions do not show an isolated compound in the expected 11B NMR range. Our goal going forward is to modify the step in the procedure where hydrazine dichloride is being added to hopefully permit the isolation of the compound so we can further study its properties.
Recommended Citation
Mann, Kenzington and Abbey, Eric, "Dehydro Coupling of Organoborohydrides to Form BN-Heterocycles" (2024). 2024 Symposium. 24.
https://dc.ewu.edu/srcw_2024/ps_2024/p1_2024/24
Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-No Derivative Works 4.0 International License.
Dehydro Coupling of Organoborohydrides to Form BN-Heterocycles
PUB NCR
Currently, there has not been a way to synthesize the potentially aromatic nitrogen-boron heterocycle (4-phenyl-1,2,3,6-tetrahydro-1,2,3,6-diazadiborine), which contains two carbons, two borons, and two nitrogen atoms. The goal of this project is to create a synthetic pathway that can be done in a “one-pot” synthesis as well as in a suitable environment to prevent the compound from degrading. There have been two procedures we have been following in efforts to produce our compound. The first procedure reacts styryl bis(BPin) with either LiAlH4 or NaAlH4 to create a styryl borohydride followed by adding hydrazine dihydrochloride. The second procedure uses styryl bis(BF3K) as the starting material rather than styryl bis(BPin) and follows the same additions. This reaction is a dehydro coupling, forming B-N bonds. The results from these reactions do not show an isolated compound in the expected 11B NMR range. Our goal going forward is to modify the step in the procedure where hydrazine dichloride is being added to hopefully permit the isolation of the compound so we can further study its properties.
