Oxidative Coupling Copolymerization of 2,6-Dimethylphenol and Dihydroxynaphthalene Affording Poly(phenylene oxide) Derivatives

Table 1

Homopolymerization of DMP or DHNs.

Run	Monomer	Catalyst	Yield
			(%)^a	(/)^b
1	DMP	CuCl-BPy^c,d	70	19.1 (2.5)
2	DMP	CuCl(OH)-TMEDA	77	72.6 (4.9)
3	2,3-DHN	CuCl-BPy^c	28^e	17.0 (1.3)
4	2,3-DHN	CuCl(OH)-TMEDA	97^e	6.4 (1.6)
5	2,6-DHN	CuCl-BPy^c,d	88^e	—^f
6	2,6-DHN	CuCl(OH)-TMEDA^d	33^e	—^f

Conditions: [monomer]/[Cu] = 10/1, solvent = DCM-MeOH (7/1, v/v), time = 48 h, temp. = r.t., and O₂ atmosphere.
^aMeOH-insoluble part.
^bDetermined by SEC (THF or CHCl₃, polystyrene standard).
^c[Monomer]/[Cu] = 5/1.
^dPolymerization time = 24 h.
^eMeOH-insoluble fraction of acetylated products.
^fInsoluble in THF and CHCl₃.