Presenter(s)
Ava Dillon
Abstract
trans-4-Bromo-2-heptene (1) is a simple compound that, despite two reports to the contrary, has never been synthesized in pure form. Nevertheless, it could be a useful starting material for organic synthesis. The compound presents a significant synthetic challenge due to a propensity to undergo allylic rearrangement to form a mixture of allylic bromides. Therefore, the goal of this research was to synthesize 1 with a multistep synthesis. Step 1 was to produce hept-2-yn-4-ol (2) via a Grignard synthesis by combining butanal and propynyl magnesium bromide with the triple bond acting as a masking group for the alkene. The alcohol was then converted to 4-bromo-2-heptyne (3) using triphenylphosphine, bromine, and imidazole. The most critical step of selectively reducing the triple bond to the desired double bond was attempted using both H2 and palladium on polyethylene imine catalyst and a monohydroboration method via disiamylborane and protonolysis with acetic acid. Finally, because the reduction should produce the cis alkene, the last step will be isomerization, to produce 1.
College
College of Science & Engineering
Department
Chemistry
Campus
Winona
First Advisor/Mentor
Tom Nalli
Location
Kryzsko Great River Ballroom, Winona, Minnesota; United States
Start Date
4-23-2026 1:00 PM
End Date
4-23-2026 2:00 PM
Presentation Type
Poster Session
Format of Presentation or Performance
In-Person
Session
2a=1pm-2pm
Poster Number
15
Progress Towards the Synthesis of trans-4-Bromo-2-Heptene
Kryzsko Great River Ballroom, Winona, Minnesota; United States
trans-4-Bromo-2-heptene (1) is a simple compound that, despite two reports to the contrary, has never been synthesized in pure form. Nevertheless, it could be a useful starting material for organic synthesis. The compound presents a significant synthetic challenge due to a propensity to undergo allylic rearrangement to form a mixture of allylic bromides. Therefore, the goal of this research was to synthesize 1 with a multistep synthesis. Step 1 was to produce hept-2-yn-4-ol (2) via a Grignard synthesis by combining butanal and propynyl magnesium bromide with the triple bond acting as a masking group for the alkene. The alcohol was then converted to 4-bromo-2-heptyne (3) using triphenylphosphine, bromine, and imidazole. The most critical step of selectively reducing the triple bond to the desired double bond was attempted using both H2 and palladium on polyethylene imine catalyst and a monohydroboration method via disiamylborane and protonolysis with acetic acid. Finally, because the reduction should produce the cis alkene, the last step will be isomerization, to produce 1.
Comments
Dillon, Ava L