Azetidine nitrones have been synthesized from <i>N</i>-vinylnitrones. These conrotatory 4-π-4-atom electrocyclizations are unusual due to the ring-strain installed in the forward direction and are synthetically valuable for the diastereoselective preparation of partially unsaturated azetidines that can be used for divergent derivatization and the preparation of highly-substituted azetidines. To more fully develop this method, mechanistic studies were undertaken to develop a fundamental understanding of the substituent and solvent effects in these transformations. A systematic series of Hammett, Eyring, and relative rate studies will be presented with results demonstrating the utility of these trends in understanding the process and broadening the method.

Mechanistic study of 4π-electrocyclizations of <i>N</i>-vinylnitrones

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Mechanistic study of 4π-electrocyclizations of N-vinylnitrones