title: Synthesis and reactivity of 1-substituted 2-fluoro- and 2,2-difluoroaziridines.
abstract: 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.
authors.affiliation: Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium.
authors.forename: Guido
authors.initials: G
authors.lastname: Verniest
authors.forename: Filip
authors.initials: F
authors.lastname: Colpaert
authors.forename: Eva
authors.initials: E
authors.lastname: Van Hende
authors.forename: Norbert
authors.initials: N
authors.lastname: De Kimpe
mesh_terms: D001388:Aziridines / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
chemical_list: D001388:Aziridines; D006845:Hydrocarbons, Fluorinated