Title
Synthesis and reactivity of alkenyl- and alkynyl-substituted, <tex>$\beta$</tex>,<tex>$\beta$</tex>-dihalo-and <tex>$\beta$</tex>,<tex>$\beta$</tex>,<tex>$\beta$</tex>-trichloroaminesSynthesis and reactivity of alkenyl- and alkynyl-substituted, <tex>$\beta$</tex>,<tex>$\beta$</tex>-dihalo-and <tex>$\beta$</tex>,<tex>$\beta$</tex>,<tex>$\beta$</tex>-trichloroamines
Author
Faculty/Department
Faculty of Sciences. Chemistry
Publication type
article
Publication
Oxford,
Subject
Chemistry
Source (journal)
Tetrahedron. - Oxford
Volume/pages
65(2009):10, p. 1957-1966
ISSN
0040-4020
ISI
000263945800003
Carrier
E
Target language
English (eng)
Full text (Publishers DOI)
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.
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