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- Title
Substituent and Solvent Effect Studies of N‐Alkenylnitrone 4π Electrocyclizations.
- Authors
Alonso, Laura; Shevlin, Michael; Alshreimi, Abdullah S.; Reidl, Tyler W.; Wink, Donald J.; Anderson, Laura L.
- Abstract
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 the 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.
- Subjects
LINEAR free energy relationship; ACTIVATION energy; SOLVENTS; RING formation (Chemistry); NITRONES; AZETIDINE
- Publication
Chemistry - A European Journal, 2023, Vol 29, Issue 30, p1
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.202300551