Substituent effect on the mechanism of alkaline hypochlorite oxidations of 2-nitroanilines & structural determination of agnotobenzaldehyde

Abstract

This thesis presents two separate topics, which contain their own compound numbering schemes. Each part starts compound numbering with 1 and progresses independently. Benzofurazan 1-oxides and azobenzenes are both types of compounds that are of developing interest for their potential medical and material applications, respectively. Benzofurazan 1-oxides have many positive medicinal applications allowing them to potentially enhance the way current drugs work. Alternately, azobenzenes are of developing interest as molecular switches that could be used to develop nano-circuitry due to their ability to change conductivity through photo-induced isomerism. Both of these molecules are co-products in the hypochlorite oxidation of 2-nitroanilines; this study investigates the effect of varying functional groups at differing aromatic positions to determine what effects they have and proposes a mechanism that fits the observations. “Agnotobenzaldehyde” was a solid isolated by Eugen Bamberger from the attempted reduction of 2-nitrobenzaldehyde to 2-nitrosobenzaldehyde. Though there has been some work over the years to attempt to determine the structure of agnotobenzaldehyde, the actual structure of agnotobenzaldehyde has remained a mystery for 104 years. This thesis presents the history of agnotobenzaldehyde, the reasons for the difficulty in determining its structure, and its final structural elucidation