Isoxazolines, acylaziridines, and oxazolines have found applications as biologically active compounds, ligands, polymer subunits, protecting groups, and in natural product synthesis. As originally disclosed by Baldwin and co-workers in 1968, 4-isoxazolines are prone to rearrangements to 2-acylaziridines and subsequently to 4-oxazolines. A better understanding of the mechanism and electronics of this transformation could inform reaction design and scope. This could allow for the synthesis of more stable isoxazolines, acylaziridines, and oxazolines and potentially an increased diversity of rearrangement products.<br/>Presented here are the results of a computational (DFT) study for this series of transformations. We have examined the electronics of these molecules, including the thermally unstable N-O bond present in 4-isoxazolines. Reaction coordinate diagrams including key transition states were also determined.

Computational study of 4-isoxazolines, 2-acylaziridines, and 4-oxazolines rearrangements

255th National Meeting (2018)

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