Synthesis and reactivity of 3-(2-chloroalkyl)-2,2-dihaloaziridines

Add time:09/07/2019    Source:sciencedirect.com

3-(2-Chloroalkyl)-2,2-dihaloaziridines were synthesized via cycloaddition of dihalocarbenes to the CN double bond of β-chloroimines. Under the action of Lewis acids or HCl, N–C3 bond cleavage occurred, giving rise to N-substituted 2,4-dichloro-3,3-dimethylbutanamides, which were further converted to 3-chloropyrrolidin-2-ones under alkaline conditions. When 2,2-dichloro-3-(2-chloro-1,1-dimethylethyl)-1-phenylaziridine was reacted with sodium methoxide, aziridine ring opening with N–C2 bond cleavage took place, leading to methyl 4-chloro-3,3-dimethyl-2-(phenylamino)butanoate.

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