Polyhalogenoaromatic compounds. Part XX. Some reactions of decachlorobiphenyl

Abstract

Decachlorobiphenyl is reduced at the 4,4′-positions when treated with excess of lithium aluminium hydride, n-butyl lithium, or magnesium followed by hydrolysis. With molar proportions of these reagents inseparable mixtures of mono- and di-substituted compounds were obtained. The lithio-derivatives were converted into the methyl derivatives with dimethyl sulphate, and also underwent thermal elimination of LiCl to give the corresponding arynes. The title compound reacted readily with both piperidine and methoxide to give the 4- and 4,4′-substituted polychlorobiphenyls. Oxidation of the piperidino-derivatives gave the corresponding nitro-compounds.