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Margarita Wickham
Chemistry

Mike Haley, Mentor

The Cyclization of 2-(Phenylazobenzonitriles)

This research explores a new route to synthesize isoindazoles through the cyclization of 2-(phenylazo)benzonitriles. A series of unique isoindazoles have been rationally designed and synthesized through this method. The neutral conditions allow for new patterns of substitution as yet unreported in the literature. In an effort toward understanding the mechanism behind this synthesis, we have trapped the intermediate with the addition of electron-rich alkenes to produce aziridines. Through spectral analysis we have determined that the intermediate is a nitrene, analogous to the carbene we observed for the 2-(alkylphenyl)diazenes previously studied. This singlet nitrene demonstrates stereospecificity.