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Issue 19, 1969
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Polyhalogenoaromatic compounds. Part VIII. Reaction of aryl-lithium compounds with tetrachloro-4-methoxypyridine, and of aryl-substituted polychloropyridines with n-butyl-lithium

Abstract

The reaction of phenyl-lithium with tetrachloro-4-methoxypyridine gave, successively, tetrachloro-4-phenylpyridine, trichloro-4,6-diphenylpyridine, and dichloro-2,4,6-triphenylpyridine; under mild conditions, p-methoxyphenyl-lithium, p-dimethylaminophenyl-lithium, and p-trifluoromethylphenyl-lithium gave the corresponding 4-aryltetrachloropyridines. With n-butyl-lithium, the 4-aryl-tetrachloropyridines gave the corresponding 4-aryltrichloro-3-pyridyl-lithium compounds. Attempts to trap 2-pyridynes generated by elimination of lithium chloride from the 3-pyridyl-lithium compounds were largely unsuccessful; with furan, the main products were the 4-aryl-2,3,6-trichloropyridines, but with trichloro-4-phenyl-3-pyridyl-lithium, a small amount of 2,3-dichloro-5,8-epoxy-5,8-dihydro-4-phenylquinoline was obtained.

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Article information


J. Chem. Soc. C, 1969, 2376-2378
Article type
Paper

Polyhalogenoaromatic compounds. Part VIII. Reaction of aryl-lithium compounds with tetrachloro-4-methoxypyridine, and of aryl-substituted polychloropyridines with n-butyl-lithium

J. D. Cook and B. J. Wakefield, J. Chem. Soc. C, 1969, 2376
DOI: 10.1039/J39690002376

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