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

Table 3

Copolymerization between DMP and DHNs with CuCl(OH)-TMEDA.

Run	Comonomer	Feed ratio	Yield	Unit ratio
		DMP : DHN derivative	(%)^a	DMP : DHN^b	()^c
1	MeDHN	50 : 50	6	—	—
2	MeDHN	70 : 30	11	96 : 4	—
3	2,7-DHN	50 : 50	34	87 : 13	10.0 (2.0)
4	MDHNA^d	70 : 30	96	58 : 42	10.8 (1.6)

Conditions: [monomers]/[Cu] = 10/1, solvent = THF, time = 24 h, temp. = r.t., and O₂ atmosphere.
^aMeOH-insoluble part of the products after phenylacetylation.
^bDetermined by ¹H NMR analysis (CDCl₃).
^cDetermined by SEC (THF, polystyrene standard).
^dSolvent = DCM-MeOH (7/1, v/v).