Defense Date

4-1-2021

Graduation Date

Spring 5-7-2021

Availability

Immediate Access

Submission Type

thesis

Degree Name

MS

Department

Chemistry and Biochemistry

Committee Chair

Aaron Bloomfield

Committee Member

Thomas Montgomery

Committee Member

Jeffrey Evanseck

Committee Member

Elizabeth Brown

Keywords

Mitsunobu Reaction, Organocatalyst, Elimination-addition, Addition-rearrangement, Redox-neutral, Computational, Secondary Phosphine Oxides

Abstract

The purpose of this thesis was the identification of a more efficient catalyst analog that could perform the redox-neutral Mitsunobu reaction, which was achieved via two synthetic pathways: elimination-addition and addition-rearrangement. Furthermore, a computational investigation was conducted on the conflicting interpretations of the catalytic cycle. Our research group replicated Houk et al. work, as well as expanded the computations to examine the influence different functional groups had on the ground state and transition state structures. Important ground state and transition state structures were determined, which provided a more energetically favorable pathway of the catalytic cycle. Experimental work demonstrated that both one-step syntheses could generate modified organocatalyst and observe the influence different functional groups had on the catalytic activity. The addition-rearrangement synthesis was determined to be the optimal pathway with yields ≥ 70%.

Language

English

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