Abstract:
The nature of the halogen dramatically affects the properties of azomethine ylides derived from dihalocarbenes and the benzophenone Schiff bases of amino acid esters: dichloro- and chlorofluoroylides cyclise to give gem-dihaloaziridines 2a–e, while difluoroylides characteristically undergo ylide–ylide isomerisation and 1,3-dipolar cycloaddition.