Date of Award
4-30-2021
Document Type
Thesis
Degree Name
Bachelor of Science
Department
Chemistry
First Advisor
Dr. Emma Goldman
Second Advisor
Dr. Raymond Dominey
Abstract
Beta-chloroenals are readily accessible substances and are efficient precursors for a variety of heterocyclic compounds. Suzuki type cross-coupling reactions of such compounds with arylboronic acids yield ��,��-diarylacroleins with control of stereochemistry. The oxidation of these enals to the corresponding acids and subsequent oxidative lactonization leads to formation of the respective coumarins. The chemistry involved in these transformations with special attention to stereochemistry of the Suzuki coupling reaction will be discussed. A full NMR analysis involving 1H, 13C, COSY, NOESY, HSQC, and HMBC was performed to unambiguously confirm the structure and show that the reaction proceeds with retention of stereochemistry.
Recommended Citation
Carrick, William, "Stereochemical Control in Suzuki Cross Coupling Reactions of Acyclic (Z)-beta-haloacroleins" (2021). Honors Theses. 1591.
https://scholarship.richmond.edu/honors-theses/1591