Ta. Luther et al., Synthesis and characterization of poly{hexakis[(methy1)(4-hydroxyphenoxy)]cyclotriphosphazene}, J APPL POLY, 82(14), 2001, pp. 3439-3446
The reaction of methylhydroquinone with hexachlorocyclotriphosphazene in th
e presence of a base, 4-picoline, in cyclohexane was investigated. Nuclear
magnetic resonance spectroscopy, multiangle laser light scattering, and ele
mental analyses were performed on the product and two other related phospha
zene materials produced by analogous synthetic routes: poly[hexakis(4-hydro
xyphenoxy)cyclotriphosphazene] (1) and hexakis[(3-tert-butyl)(4-hydroxyphen
oxy)]cyclotriphosphazene (2). Unlike the data for 2 where the tert-butyl mo
iety enforced regiospecific nucleophilic addition, the data for the methylh
ydroquinone-substituted cyclotriphosphazene product indicate that the less
sterically bulky methyl group provides only limited protection for the adja
cent hydroxyl group. The result is the formation of a low molecular weight
oligomer, poly(hexakis[(methyl)(4-hydroxyphenoxy)]cyclotriphosphazene) (3),
instead of a discrete cyclic trimer species. (C) 2001 John Wiley & Sons, I
nc.