Direct metalation of poly(2,6‐dimethyl‐1,4‐phenylene ether)

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Abstract
Poly(2,6‐dimethyl‐1,4‐phenylene ether) (I) was metalated with butyllithium in tetrahydrofuran and with the N,N,N′,N′‐tetramethylethylenediamine complex of butyllithium in a variety of solvents. In these cases, metalation occurred at both the ring and side chain positions, the former being preferred initially. Subsequently, there was an isomerization in favor of the side chain. magnified image At 25°C, there is no significant amount of polymer scission or crosslinking during metalation, but some crosslinking occurs on derivatizing with dimethyl sulfate and trimethylchlorosilane for high extents of ring metalation. With sodium and potassium alkyls, only side‐chain metalation was observed. The metalated polymer reacts as a typical organometallic, allowing polymer modification by a wide variety of reactions.