Date of Award

2019

Degree Name

Chemistry

College

College of Science

Type of Degree

M.S.

Document Type

Thesis

First Advisor

Dr. Michael Castellani

Second Advisor

Dr. Robert Morgan

Third Advisor

Dr. John Markiewicz

Abstract

Although isoelectronic to benzene, the reactivity of pyridine-derived compounds can be quite different. Notably, routes to prepare pyridyl analogs to known phenyl compounds can be very different from how the phenyl compounds are made, even when the nitrogen atom would appear to play an insignificant role in the reaction. This is the case for 1,3-di-4-pyridylacetone. Its phenyl analog has been known for over 90 years and is easily prepared, while the only reported synthesis of 1,3-di-4-pyridylacetone occurs in very low yield. We report a preliminary synthesis from common starting materials, albeit in low yield, and offer an explanation for why previous preparations were unsuccessful and how yields could be improved.

Subject(s)

Phenyl compounds.

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