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Paper | Regular issue | Vol 38, No. 11, 1994, pp.2481-2486
Published online, 1st January, 1970
DOI: 10.3987/COM-94-6885
Reaction of Pentachloropyridine 2,3,4,5-Tetrachloro-4-pyridyllithium with α-Lithiated Arylacetonitriles and N-Butyllithium

Edward R. Biehl,* Hala Mohammed Rafat, and A. A. Fadda

*Department of Chemistry, Southern Methodist University, P.O. Box 750314, Dallas, TX 75275-0314, U.S.A.

Abstract

Perchloropyridine (1) reacts smoothly at -70 °C with α-lithioarylacetonitriles (3) affording α-(aryl)-2,3,5,6-tetrachloro-4-pyridylacetonitriles (4). The 2,5,6-trichloro-3,4-dehydropyridine precursor, 2,3,5,6-tetrachloropyridyllithium (5), reacts similarly at -70 °C with 3, but instead of providing 3,4-dehydropyridine products, α-(aryl)-2,3,4,5-tetrachlorophenylacetonitrile supplies mainly 4 and α-(aryl)-3,5,6-trichloro-2-pyridylacetonitriles (6) plus minor quantities of α-(aryl)-3,4,5,6-tetrachloro-2- (7) and α-(aryl)-2,4,5,6-tetrachloro-3-pyridylacetonitriles (8). The product ratios of 4 to 6 from these reactions as well as the relative yields of 4 from the reaction of 1 and 5 with 3 are highly dependent upon 3. To account for these results, an explanation in terms of competing lithium-chlorine exchanges between 1 or 5 with 3 of α-chloroarylacetonitriles (9) is proposed.