PhICl₂-Mediated Conversion of Enamines into α,N-Dichloroimines and Their Reverse Conversion Mediated by Zinc in Methanol

Abstract

Treatment of enamine compounds with iodobenzene dichloride (PhICl₂) conveniently gives a variety of α,N-dichloroimines in high yields. This approach allows the double insertion of the chloro moiety, which is postulated to take place via the iodobenzene dichloride mediated oxidative α-chlorination of the enamine substrates followed by further N-chlorination of the imine intermediates. Furthermore, the obtained α,N-dichloroimines could be converted reversely into the original enamines under reductive conditions using zinc in methanol.

Key words

enamines - iodobenzene dichloride - α,N-dichloroimines - chlorination - zinc

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