Metal-free thioketene-induced ring expansion of aziridines gave 4-alkylthiazolines stereospecifically from 2-alkylaziridines through an intramolecular substitution at the less substituted ring carbon and 5-arylthiazolines stereoselectively from 2-arylaziridines via tandem ring cleavage… Click to show full abstract
Metal-free thioketene-induced ring expansion of aziridines gave 4-alkylthiazolines stereospecifically from 2-alkylaziridines through an intramolecular substitution at the less substituted ring carbon and 5-arylthiazolines stereoselectively from 2-arylaziridines via tandem ring cleavage and formation through intimate ion-pair intermediates after nucleophilic addition of aziridines to thioketenes generated from 4-substituted 1,2,3-thiadiazoles in the presence of a base.
Journal Title: Chemical communications
Year Published: 2022
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