Substituent and Solvent Effect Studies of N-Alkenylnitrone 4π Electrocyclizations.
Chemistry
; 29(30): e202300551, 2023 May 26.
Article
in En
| MEDLINE
| ID: mdl-36840693
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.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Type of study:
Prognostic_studies
Language:
En
Journal:
Chemistry
Journal subject:
QUIMICA
Year:
2023
Document type:
Article
Affiliation country:
Estados Unidos