Title
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Synthesis and reactivity of alkenyl- and alkynyl-substituted, ,-dihalo-and ,,-trichloroamines
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Author
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Abstract
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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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Language
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English
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Source (journal)
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Tetrahedron. - Oxford, 1957, currens
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Publication
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Oxford
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2009
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ISSN
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0040-4020
[print]
1464-5416
[online]
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DOI
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10.1016/J.TET.2009.01.034
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Volume/pages
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65
:10
(2009)
, p. 1957-1966
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ISI
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000263945800003
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Full text (Publisher's DOI)
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Full text (publisher's version - intranet only)
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