Substituent and Solvent Effect Studies of N-Alkenylnitrone 4π-Electrocyclizations

20 December 2022, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


The roles of substituent and solvent effects in promoting the 4π-electrocyclization of N-alkenylnitrones to give azetidine nitrones have been investigated by experimental examination of relative rates, activation energies, and linear free energy relationships. These transformations are synthetically important because they favor formation of a strained heterocyclic ring with imbedded functionality and stereochemical information for versatile derivatization. Mechanistic investigations, including Hammett studies, solvent-dependent Eyring studies, and solvent isotope effects, provide insight into the steric and electronic factors that control these electrocyclizations and identify trends that can be used to advance this approach towards the rapid synthesis of complex azetidines.


mechanism study
substituent effects
solvent effects
azetidine nitrone

Supplementary materials

Supporting Information for "Substituent and Solvent Effect Studies of N-Alkenylnitrone 4π-Electrocyclizations"
Materials and methods for the experiments described.


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