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Synthesis and reactivity of 1-substituted 2-fluoro- and 2,2-difluoroaziridines. 2007

Guido Verniest, and Filip Colpaert, and Eva Van Hende, and Norbert De Kimpe
Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium.

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.

UI MeSH Term Description Entries
D003500 Cyclization Changing an open-chain hydrocarbon to a closed ring. (McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Cyclizations
D006845 Hydrocarbons, Fluorinated Inert liquid or gaseous halocarbon compounds in which FLUORINE replaces some or all HYDROGEN atoms. Fluorinated Hydrocarbons
D001388 Aziridines Saturated azacyclopropane compounds. They include compounds with substitutions on CARBON or NITROGEN atoms. Ethyleneimines,Azacyclopropanes, Saturated,Dimethyleneimines,Saturated Azacyclopropanes
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular

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