Date of Award
10-16-2023
Degree Type
Dissertation
Degree Name
Doctor of Philosophy (PhD)
Department
Chemistry
First Advisor
James Devery
Abstract
Lewis acids have proven extremely valuable to the field of organic synthesis. Their diverse application in reactions of carbonyl-containing substrates has caused a multitude of efforts towards characterization of solution interactions between Lewis bases and Lewis acids. Though Lewis initially described a 1:1 interaction between one acid and one base, our lab has previously employed in-situ IR spectroscopy to characterize 2:1, 3:1, and 4:1 solution structures under catalytic conditions. These insights have played a critical role in our understanding of catalyst behavior in carbonyl-containing systems, allowing us to describe byproduct inhibition in the carbonyl-olefin metathesis mechanism. The research presented in this dissertation suggests that solution interactions between Lewis acids and carbonyls can be altered with the use of ligands or additives. This change in solution behavior may also result in differing catalytic reactivity in organic systems. Using in-situ IR spectroscopy and conductivity measurements, I will detail the effect of ligands and additives on the interactions of carbonyls and Lewis acids. Experiments designed to examine the impact of these changes in solution behavior on catalytic systems will be presented. Additionally, a new synthetic method towards the construction of 3.3.1 bicyclononene compounds employing a 4:1 carbonyl:FeCl3 catalyst will be described.
Recommended Citation
Todtz, Sophi Rose, "Interactions of Lewis Acids and Carbonyls in the Presence of Ligands Or Additives: How Solution Behavior Differs and the Implication on Catalytic Systems" (2023). Dissertations. 4044.
https://ecommons.luc.edu/luc_diss/4044
