Synthesis and reactivity of alkenyl- and alkynyl-substituted, <script type="math/tex">\beta</script>,<script type="math/tex">\beta</script>-dihalo-and <script type="math/tex">\beta</script>,<script type="math/tex">\beta</script>,<script type="math/tex">\beta</script>-trichloroamines

Abbaspour Tehrani, Kourosch; Stas, Sara; Lucas, Bart; De Kimpe, Norbert

doi:10.1016/J.TET.2009.01.034

Title

Synthesis and reactivity of alkenyl- and alkynyl-substituted, $\beta$ , $\beta$ -dihalo-and $\beta$ , $\beta$ , $\beta$ -trichloroamines

Author

Abbaspour Tehrani, Kourosch

Stas, Sara

Lucas, Bart

De Kimpe, Norbert

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