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Paper | Regular issue | Vol 41, No. 2, 1995, pp.289-292
Published online, 1st January, 1970
DOI: 10.3987/COM-94-6912
Reaction of Pentachloropyridine with α-Lithiated Arylacetonitriles and Methyllithium in Ether

Edward R. Biehl*, Hala Mohammed Refat, and Amamed A. Fadda

*Department of Chemistry, Southern Methodist University, Dallas, TX 75275, U.S.A.


Ether slurries of α-lithioarylacetonitriles (3) when added to ether solutions of 2,3,5,6-tetrachloro-4-pyridyllithium (2) at -70°C give clear, red solutions upon warming to -20°C. Further warming to room temperature, produces bright scarlet precipitates which upon proton quench provide α-aryl-2,3,5,6-tetrachloro-4-pyridylacetonitriles (4) in excellent yields (98-80%). A mechanism is proposed in which the key step involves a lithium-chlorine exchange between 2 and α-lithio-α-chloroarylacetonitriles (7). Experimental evidence for the intermediacy of 7 in these reactions is presented.