Thesis Title

Reactivity of the Vinylogous Epoxyketone Moiety

Date of Graduation

Summer 1996

Degree

Master of Science in Chemistry

Department

Chemistery

Committee Chair

Tamera Jahnke

Subject Categories

Chemistry

Abstract

The lipid peroxidation process produces lipid hydroperoxides which decompose to a variety of secondary lipid peroxidation products such as epoxides, aldehydes, and ketones. A vinylogous epoxyketone, 5,6-epoxy-3-nonen-2-one was chosen as a model of one lipid oxidation product. The synthesis and characterization of the model are presented. The reactivity of the model was predicted from molecular orbital calculations and the hard and soft acid base (HSAB) theory. These results are compared to experimental results obtained from adding various nucleophiles. A hard nucleophile, phenyl lithium, was shown to add according to predications based on the HSAB theory. The reactivity of a soft nucleophile, the enolate of diethyl malonate, was not explained by the HSAB theory but by other factors such as ring strain and steric hindrance of the epoxide ring.

Copyright

© Robert Scott Martin

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