- Polyhalogenoaromatic Compounds. Part 44. Reactions of Enamines with Polyhalogenopyridines and their N-Oxides
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1-Dialkylaminocyclohexenes were readily C-arylated by pentafluoropyridine or 3,5-dichlorotrifluoropyridine but pentachloropyridine was much less reactive.The resulting (tetrahalogenopyridyl)enamines did not cyclise on heating except in the case of compound (10), which gave the heterocycle (16). 1-Dialkylaminocycloalkenes and other enamines were C-arylated by pentachloropyridine N-oxide.In the cases of the dialkylaminocyclo-hexenes and -heptenes the expected pyridylenamines were accompanied by 1-(tetrachloro-2-pyridyl)cyclo-pentene and -hexene, respectively.A mechanism for the ring-contraction leading to the pyridylcycloalkenes is proposed involving a novel elimination of an N-formyldialkylamine.
- Suschitzky, Hans,Wakefield, Basil J.,Whitten, Jeffrey P.
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p. 2709 - 2716
(2007/10/02)
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- Condensation of αβ-unsaturated amines with perfluoroarenes
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Condensation of αβ-unsaturated amines (enamines, keten ON-acetals, ynamines) with perfluoroarenes (perfluorobenzene, perfluorotoluene, bromopentafluorobenzene, perfluoropyridine) leads to the formation of ketones, esters, and amines α-substituted by a perfluoroaryl group. In the case of enamines, C-arylation can be followed by intramolecular N-arylation, giving fluorinated tetrahydrocarbazoles which can then be dehydrogenated by chloranil to give fluorinated carbazoles.
- Blazejewski, Jean-Claude,Wakselman, Claude
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p. 2845 - 2850
(2007/10/02)
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