Synthesis and reactivity of 1-substituted 2-fluoro- and 2,2-difluoroaziridines.
A straightforward synthesis toward 2-fluorinated aziridines was developed via ring closure of beta-fluorinated beta-chloroamines, which were obtained via reduction of the corresponding alpha-fluorinated amides by borane. When 1-benzyl-2-fluoroaziridine was treated with methanol, reaction occurred at the 2-position, giving rise to N-benzyl-2,2-dimethoxyethylamine, while in the case of 1-benzyl-2,2-difluoroaziridine the 3-position was attacked, giving rise to N-benzyl-2-methoxyacetamide. These reactions point to the divergent reactive behavior of monofluoro- and difluoroaziridines.
Verniest
Guido
G
Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium.
Colpaert
Filip
F
Van Hende
Eva
E
De Kimpe
Norbert
N
D001388:Aziridines / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
D001388:Aziridines; D006845:Hydrocarbons, Fluorinated