Date Written

2015

Document Type

Honors Paper

Degree Name

Chemistry-BS

Department

Chemistry

Advisor

Robin Grote, Ph.D.

First Committee Member

Robin Grote, Ph.D.

Second Committee Member

Carrigan Hayes, Ph.D.

Third Committee Member

Jessica Crossfield McIntosh

Keywords

Chemistry, Organic, Synthesis, Catalysis, Gold, Heterocycles

Subject Categories

Organic Chemistry

Abstract

The goal of this project was to study novel synthetic procedures for heterocycles. This was achieved through a two-part investigation. In the first part, a variety of conditions for the gold catalyzed cyclization of allenes were studied. This work was focused on the lesser studied intermolecular reactions of allenes. A variety of allenes were synthesized, and then reacted with 1,3-dipoles and a gold catalyst. These reactions were determined to be unsuccessful through the analysis of nuclear magnetic resonance spectroscopy data. In the second part of this study, the synthesis of 1,3,4-oxadiazoles was investigated. Several cited procedures were examined to determine which procedure would be the highest yielding to synthesize these compounds. The chosen reactions were then completed again, placing an electron donating group or an electron withdrawing group on the phenyl ring of the final product in order to determine the effect of electronics on the yield of the products. An electrostatic potential map was generated for each 1,3,4-oxadiazole product from a computational program, and was then used to analyze the distribution of charge across the molecule. These maps were then used to study the effect of the electronics on the yield of the product, but the results were inconclusive.

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