Publication
Title
Synthesis and reactivity of alkenyl- and alkynyl-substituted, ,-dihalo-and ,,-trichloroamines
Author
Abstract
beta,beta-Dihalo and beta,beta,beta-trichloroamines, obtained by Lewis acid-promoted Petasis-type reaction of alpha,alpha-dichlorinated and alpha,alpha,alpha-trichlorinated imines or reduction of alpha,alpha-dihaloaldimines, were subjected to a reactivity study and turned out to be remarkably stable compounds. In general, only the bases KO'Bu and NaOMe cause a 1,2-dehydrochlorination with formation of unsaturated alpha-chloroimines Or Unsaturated alpha,alpha-dichloroimines. Hydrolysis of the alpha-chloroimines with aqueous oxalic acid resulted in the formation of the corresponding unsaturated alpha-chloroketones. The reaction of simple beta,beta-dihaloamines with NaOMe and KO'Bu generated 2-haloprop-2-enylmines and 2,2-dimethoxypropylamines. (C) 2009 Elsevier Ltd. All rights reserved.
Language
English
Source (journal)
Tetrahedron. - Oxford, 1957, currens
Publication
Oxford : 2009
ISSN
0040-4020 [print]
1464-5416 [online]
DOI
10.1016/J.TET.2009.01.034
Volume/pages
65 :10 (2009) , p. 1957-1966
ISI
000263945800003
Full text (Publisher's DOI)
Full text (publisher's version - intranet only)
UAntwerpen
Faculty/Department
Publication type
Subject
External links
Web of Science
Record
Identifier
Creation 28.01.2013
Last edited 20.08.2024
To cite this reference