TY - JOUR

T1 - Synthesis and reactivity of 3-(2-chloroalkyl)-2,2-dihaloaziridines

AU - Shinkevich, Ekaterina Yu

AU - Tehrani, Kourosch Abbaspour

AU - Khlebnikov, Alexander F.

AU - Novikov, Mikhail S.

PY - 2008/8/4

Y1 - 2008/8/4

N2 - 3-(2-Chloroalkyl)-2,2-dihaloaziridines were synthesized via cycloaddition of dihalocarbenes to the C{double bond, long}N 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.

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

KW - Aziridines

KW - Cyclizations

KW - Dihalocarbenes

KW - Selective ring opening

UR - http://www.scopus.com/inward/record.url?scp=45649083919&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2008.05.121

DO - 10.1016/j.tet.2008.05.121

M3 - Article

AN - SCOPUS:45649083919

VL - 64

SP - 7524

EP - 7530

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 32

ER -