Abstract

Preparation of Complexes as Robust Catalytic Oxidants

Student: Colleen Chernowsky
Mentor: Kim Lance (Department of Chemistry)

Current chemical reactions used in water purification produce byproducts harmful to the environment and to humans. Nature can do the same thing but without the production of toxic materials by using a molecule that can carry out more efficient reactions. We are working on making a molecule similar in structure to the ones used by nature in order to apply these efficient reactions to water purification processes. This will allow us to purify water on an industrial scale without producing harmful toxins.

Attempted synthesis of the compound described in Figure 1 was carried out by reacting BOC-protected o-phenylenediamine with 2,4-dibromo-2,4-dimethyl-3-pentanone and sodium hydride. An additional reaction of BOC-protected o-phenylenediamine with 2,4-dibromo-2,4-dimethyl-3-pentanone and silver oxide catalyst was carried out. Isolation of both products followed by NMR analysis showed the reactions to be unsuccessful. A repeat of both reactions with unprotected o-phenylenediamine also proved unsuccessful. A repeat of both reactions with 2-nitroanaline rather than o-phenylenediamine also proved unsuccessful. Synthesis of the compound described in Figure 1 was again attempted by reacting BOC-protected o-phenylenediame with dimethylmalonyl dichloride. Analysis of the product by NMR proved the reaction to be a success and demonstrated progress toward the synthesis of Figure 1.