Publication
Title
Synthesis and reactivity of 3-(2-chloroalkyl)-2,2-dihaloaziridines
Author
Abstract
3-(2-Chloroalkyl)-2,2-dihaloaziridines were synthesized via cycloaddition of dihalocarbenes to the C=N double bond of (3-chloroimines. Under the action of Lewis acids or HCl, N-C(3) 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-C(2) bond cleavage took place, leading to methyl 4-chloro-3,3-dimethyl-2-(phenylamino)butanoate. (C) 2008 Elsevier Ltd. All rights reserved.
Language
English
Source (journal)
Tetrahedron. - Oxford
Publication
Oxford : 2008
ISSN
0040-4020
Volume/pages
64:32(2008), p. 7524-7530
ISI
000257912200008
Full text (Publisher's DOI)
Full text (publisher's version - intranet only)
UAntwerpen
Faculty/Department
Publication type
Subject
External links
Web of Science
Record
Identification
Creation 28.01.2013
Last edited 09.06.2017