Synthesis and reactivity of alkenyl-and alkynyl-substituted β, β-dihalo-and β, β, β-trichloroamines

KA Tehrani, S Stas, B Lucas, N De Kimpe

Index: Abbaspour Tehrani, Kourosch; Stas, Sara; Lucas, Bart; De Kimpe, Norbert Tetrahedron, 2009 , vol. 65, # 10 p. 1957 - 1966

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Citation Number: 20

Abstract

β, β-Dihalo-and β, β, β-trichloroamines, obtained by Lewis acid-promoted Petasis-type reaction of α, α-dichlorinated and α, α, α-trichlorinated imines or reduction of α, α- dihaloaldimines, were subjected to a reactivity study and turned out to be remarkably stable compounds. In general, only the bases KOtBu and NaOMe cause a 1, 2-dehydrochlorination with formation of unsaturated α-chloroimines or unsaturated α, α-dichloroimines. ...