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The reactivity of stereochemically defined 3-aryl-2-chloro-2-imidoylaziridines, an unexplored class of substituted aziridines, was investigated under various reaction conditions. 2-Chloro-2-imidoylaziridines underwent a novel thermal rearrangement by reflux in acetonitrile via C–C bond cleavage to 4-chloro-2,5-diarylimidazoles in high yield. Alternatively, a novel efficient entry toward 2-aroyl-2-chloroaziridines...
Treatment of α,δ-dichloroaldimines, prepared via α-chlorination with N-chlorosuccinimide of the corresponding δ-chloroaldimines, with potassium carbonate in methanol led to the formation of 1-alkyl-2-(dimethoxymethyl)pyrrolidines in good yields. The reaction mechanism involved a skeletal rearrangement of the α,δ-dichloroaldimines to give bicyclic aziridinium intermediates which suffered ring opening...
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