Reactions of poly(phenylene oxide)s with quinones. I. The quinone‐coupling reaction between low‐molecular‐weight poly(2,6‐dimethyl‐1,4‐phenylene oxide) and 3,3′,5,5′‐tetramethyl‐4,4′‐diphenoquinone

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Abstract
A bifunctional polymer is formed when low‐molecular‐weight poly(2,6‐dimethyl‐1,4‐phenylene oxide) (I) reacts with 3,3′,5,5′‐tetramethyl‐4,4′‐diphenoquinone (II). Infrared (IR), nuclear magnetic resonance (NMR), and gel permeation chromotography (GPC) measurements indicate that the quinone is bound covalently to the polymer chain as a biphenyl moiety which can be located at a terminal position (III, a = 0) or an internal position (III, a > 0): magnified image Acetylation of III produces a diacetate ester characterized by field desorption mass spectrometry to confirm the bifunctional nature of III. The reaction of I with II proceeds at 25°C but is faster at elevated temperatures or with amine catalysis. Oxidation of III with oxygen and a copper/amine catalyst of the type used initially to prepare I regenerates II from the biphenyl moiety in III in high yield and converts the remaining oxyphenylene units to high‐molecular‐weight polymer.