Advisor

Emerson, Joseph P.

Other Advisors or Committee Members

Stokes, Sean L.||Cui, Xin||Scott, Colleen N.

Date of Degree

8-1-2019

Original embargo terms

Complete Embargo 1 Year||8/15/2020

Document Type

Graduate Thesis - Open Access

Major

Chemistry

Degree Name

Master of Science

College

College of Arts and Sciences

Department

Department of Chemistry

Abstract

Aziridines are important building blocks for the synthesis of a wide range of organic compounds, including biologically active compounds and pharmaceuticals. The development of more cost-effective catalysts for atom transfer reactions is a continuing area of research in chemistry. Transition metal complexes have been shown to catalyze the aziridination of olefins, however, most require expensive metal ions or complex ligands. Meso-tetra(N-methyl-4-pyridyl)porphyrin (TMPyP4) is a highly charged, planar ligand that has been used to support manganese(III) in complexes like Mn[TMPyP4]I5. Herein we report the optimization of the reaction conditions for the aziridination of olefins in water and buffered solutions catalyzed by Mn[TMPyP4]I5. The reaction conditions optimized include pH range, temperature, and reaction time. Additionally, nitrogen sources, nitrogen source/olefin ratios, and catalyst loading were optimized. In buffered solutions, Mn[TMPyP4]I5 can effectively catalyze the generation of aziridines from various aromatic and aliphatic olefins with Chloramine T in moderate to good yields (43-93 %).

URI

https://hdl.handle.net/11668/14600

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