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

3-(2-Chloroalkyl)-2,2-dihaloaziridines were synthesized via cycloaddition of dihalocarbenes to the C-N double bond of beta-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.

Publication year:2008

Keywords:dihalocarbenes, aziridines, cyclizations, selective ring opening, choroimine