SynopsisTreatment of benzyl chloride with iron powder in water suspension results in the formation of benzyl radicals, which are subsequently dimerized into bibenzyl. This reaction has now been extended to p-xylylene dibromide under a set of conditions aa summarized in Table I. High yields (7040%) of poly-p-xylylene, which was identified by infrared spectrum, x-ray diffraction pattern, and other properties, were obtained with reduced iron suspended in a mixture of xylene and water (50:50) or in dimethylformamide. Zinc powder coated with nickel (Urushibara nickel CB) gave comparable yields of poly-p-xylylene, while cobalt powder or zinc-cobalt couple afforded inferior yields. Similar reaction of 0-and m-xylylene dibromides gave soluble polymers. The presence of o-xylylene aa an unstable intermediate of the polymerization of o-xylylene dibromide has been indicated by trapping this transitory hydrocarbon with antrylonitrile and with methyl acrylate as diene adducts.

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