Publication Date

April 2016

Advisor(s)

Brian Northrop

Major

Chemistry

Language

English (United States)

Abstract

Thiol-Michael reactions have become the subject of increased interest due to their “click” nature, meaning they are broadly applicable, rapid, tolerant of many different reaction conditions, and high yielding. These reactions have proven to be useful in organic materials synthesis. To gain more knowledge of specific thiol-Michael reactions which yield highly selective products in a short amount of time, an investigation of ternary reactions between a single Michael acceptor and two thiols was conducted. All possible ternary combinations of six Michael acceptors and five thiols were attempted using three initiators in two solvents. The relative ratios of each product were compared using 1H NMR spectroscopy. Results indicated a similar number of highly selective ternary combinations in both solvents. Analysis of the results of these combinations resulted in the development and optimization of quaternary reactions, involving two thiols and two Michael-acceptors, to yield only two selective products. A combination of these ternary and quaternary results might allow for the creation of large multi-functionalized pendant polymers, dendrimers, and other macromolecules with fewer intermediate steps and minimal purification.

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