Title
Synthesis and reactivity of 3-(2-chloroalkyl)-2,2-dihaloaziridines
Author
Faculty/Department
Faculty of Sciences. Chemistry
Publication type
article
Publication
Oxford ,
Subject
Chemistry
Source (journal)
Tetrahedron. - Oxford
Volume/pages
64(2008) :32 , p. 7524-7530
ISSN
0040-4020
ISI
000257912200008
Carrier
E
Target language
English (eng)
Full text (Publishers DOI)
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.
E-info
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