71602-56-7Relevant articles and documents
Polyhalogenoaromatic Compounds. Part 44. Reactions of Enamines with Polyhalogenopyridines and their N-Oxides
Suschitzky, Hans,Wakefield, Basil J.,Whitten, Jeffrey P.
, p. 2709 - 2716 (2007/10/02)
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.
