A systematic investigation into the reactivity and properties of 1,2-benzisoxazole 2-oxides was undertaken. It was found that compared to the parent 2-hydroxyketones, the 1,2-benzisoxazole 2-oxides all showed significant hypsochromic shifts of their UV spectrum. This interesting observation led to the synthesis and study of a variety of substituted benzisoxazoles to determine the effect of structure on UV absorbance. Preliminary electrochemical investigations of 3-phenyl-1,2-benzisoxazole 2-oxide have shown both oxidation and reduction pathways and both appear to involve an EC mechanism. The results of a thorough electrochemical study and mechanistic pathways will be discussed. The radical scavenging ability of the benzisoxazole 2-oxide group using a 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical assay was also investigated. Initial work has shown that the incorporation of a 1,2-benzisoxazole 2-oxide ring does have an effect on radical scavenging, however the degree of radical inhibition is highly variable. Results from a variety of 1,2-benzisoxazole 2-oxide containing compounds will be presented.

Spectroscopic, electrochemical, and radical-scavenging properties of 1,2-benzisoxazole 2-oxides

244th National Meeting (2012)

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