Presenter: Allie Mackay
Authors: Allie Mackay, Nathan Werner
Faculty Advisor: Nathan Werner
Institution: Southern Utah University
Isomerization reactions are important in synthetic and industrial syntheses. They are especially noteworthy because they are 100% efficient in the transfer of atoms from the starting material to the product. The conversion of E to Z double bond isomer is important and challenging due to high energy steric interactions between the larger, typically higher priority, substituents. One method, discovered at Southern Utah University, uses a ruthenium metal catalyst and visible light to isomerize (E)-β-bromostyrene with high stereocontrol to the Z isomer. The scope of this reaction with regard to substrates with different electronic and steric properties has yet to be studied. Here we present our investigation of the electronic effects on the efficiency of E to Z double bond isomerization reaction. Different methods have been applied to synthesize (E)-β-bromostyrene derivatives in preparation for isomerization. The E/Z ratios achieved after isomerization via visible light and Ru(byp)3Cl2 are measured using NMR. References 1. J.P. Das and S. Roy. Catalytic Hunsdiecker Reaction of α,β-Unsaturated Carboxylic Acids: How Efficient Is the Catalyst? Journal of Organic Chemistry. 67 (2002) 2. D. Hazarika and P. Phukan. TsNBr2 Promoted Decarboxylative Bromination of α,β-Unsaturated Carboxylic Acids. Elsevier. (2018)