Polycondensation of xylylene dibromides by transition metals in water suspension

Treatment 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 as summarized in Table I. High yields (70–80%) of poly...

Full description

Saved in:
Bibliographic Details
Published in:Journal of polymer science. Part A. General papers 1963-06, Vol.1 (6), p.2101-2107
Main Authors: Sisido, Keiiti, Kusano, Nobuo, Noyori, Ryôzi, Nozaki, Yôko, Simosaka, Masatosi, Nozaki, Hitosi
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Treatment 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 as summarized in Table I. High yields (70–80%) 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 o ‐ and m ‐xylylene dibromides gave soluble polymers. The presence of o ‐xylylene as an unstable intermediate of the polymerization of o ‐xylylene dibromide has been indicated by trapping this transitory hydrocarbon with acrylonitrile and with methyl acrylate as diene adducts.
ISSN:0449-2951
1542-6246
DOI:10.1002/pol.1963.100010628