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

Tijdschriftbijdrage - Tijdschriftartikel

3-(2-Chloroalkyl)-2,2-dihaloaziridines were synthesized via cycloaddition of dihalocarbenes to the C-Ndouble 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 cleavagetook place, leading to methyl 4-chloro-3,3-dimethyl-2-(phenylamino)butanoate.
Tijdschrift: Tetrahedron
ISSN: 0040-4020
Volume: 64
Pagina's: 7524-7530
Aantal pagina's: 7
Jaar van publicatie:2008
Trefwoorden:dihalocarbenes, aziridines, cyclizations, selective ring opening, choroimine
  • Scopus Id: 45649083919