Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact: purchase@heterocycles.com

Price: ¥ 4,320 (Yen only)
Period: This Article can be accessed for 7 days.

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.

Abstract

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.