Bisphenol monomer hydroquinone

CO2. CHj, CO. H . propene. isobutene, dimethyl ketene. acrolein, diallyl ether, allyl methacrylate monomer and dimer, chain fragments including anhydnde structures from side-group cydization. and an aliphatic ketone in the vidnity of unsaturation CO , SO , phenol, bisphenol S, hydroquinone. fragments of backbone, benzene sulfonic acid... 

A new double adamantyl-substituted aromatic bisphenol monomer, 4,8-bis (l-adamantly)-l,5-dihydroxynaphthalene (AdNp) was successfully S5mthesized via the Friedel-Crafts reaction as depicted Scheme 10.11, and two new PAEKs containing adamantly groups (Ad-PAENKs) were synthesized based on the new monomer of AdNp, (3-trifluoromethyl)phenyl hydroquinone (3FHQ) and 4,4 -difluorobenzophenone (D ) via the nucleophilic aromatic substitution polymerization as depicted Scheme 10.12. 

The linking structure R in the monomers include bisphenol-A, bisphenol-S, bisphenol-A6F, resorcinol, hydroquinone and dihydroxybiphenol. 

All the above procedures involve aromatic dihalides or monomers derived from aromatic dihalides that are neither always commercially available nor easily synthesized. An interesting alternative was presented by Percec et al. [69]. They investigated the Colon-type, Ni(0)-catalyzed homocoupling of substituted phenyl-enebistriflates which are easily obtained from hydroquinones or bisphenols. The polymerizations were performed in either DMF or THE The polymer yield and molecular weight of the materials obtained were shown to increase in the order OTf < Br < Cl, when the polymerization was carried out in DMF. In this solvent, the temperature had a marked effect on the polymerization yield. In contrast, in THF the molecular weight increases in the order Cl < Br < OTf, with polymerization yields increasing as the amount of Ni catalyst is increased. 

The polymerization of aryl bistriflate monomers derived from hydroquinones and bisphenols is important from a synthetic perspective. Synthetic procedures and/or methods for the preparation of a variety of substituted hydroquinones and bisphenols already exist. In most cases, these compounds can be easily converted in high yields to the corresponding bistriflates. However, the cost of the reagents necessary for this conversion has limited the application of this methodology. Reaction conditions for the polymerization of aryl bismesylates, which are much less expensive sulfonates, have recently been developed for the synthesis of high molecular weight soluble PPPs (equation 58) 194). 

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