Highly Regioselective Oxidative Polymerization of 4-Phenoxyphenol to Poly(1,4-phenylene oxide) Catalyzed by Tyrosinase Model Complexes
作者： Hideyuki Higashimura , Kiyoshi Fujisawa , Yoshihiko Moro-oka , Masaaki Kubota , Akinobu Shiga
DOI: 10.1021/JA981283M
关键词:
摘要: Abstract A highly regioselective oxidative coupling of 4-phenoxyphenol (PPL) catalyzed by tyrosinase model complexes, (hydrotris(3,5-diphenyl-l-pyrazolyl)borate) copper(II) chloride (Cu(tpzb)Cl) and (l,4,7-triisopropyl-l,4,7-triazacyclononane) dichloride (Cu(tacn)Cl 2 ), is described. The polymerization PPL oxidized an equimolar 2,2'-azobisisobutyronitrile in toluene, regarded as a system free phenoxy radical coupling, gave C-C dimers besides C-0 at the initial stage yielded polymer having no melting point. However, Cu(tpzb)Cl Cu(tacn)Cl2 under dioxygen toluene dimers, hence, poly(l,4-phenylene oxide) showing crystallinity with points.
acs.org
sci-hub.se 参考文章(17)
Allan S. Hay, Polymerization by oxidative coupling. II. Oxidation of 2,6‐disubstituted phenols Journal of Polymer Science. ,vol. 58, pp. 581- 591 ,(1962) , 10.1002/POL.1962.1205816634
W.J. Mijs, O.E. van Lohuizen, J. Bussink, L. Vollbracht, The catalytic oxidation of 4-aryloxyphenols Tetrahedron. ,vol. 23, pp. 2253- 2264 ,(1967) , 10.1016/0040-4020(67)80061-9
Nobumasa Kitajima, Kiyoshi Fujisawa, Yoshihiko Morooka, Koshiro Toriumi, .mu.-.eta.2:.eta.2-Peroxo binuclear copper complex, [Cu(HB(3,5-(Me2CH)2pz)3)]2(O2) Journal of the American Chemical Society. ,vol. 111, pp. 8975- 8976 ,(1989) , 10.1021/JA00206A062
Ryohei Ikeda, Junji Sugihara, Hiroshi Uyama, Shiro Kobayashi, Enzymatic Oxidative Polymerization of 2,6-Dimethylphenol Macromolecules. ,vol. 29, pp. 8702- 8705 ,(1996) , 10.1021/MA961055H
H.M. van Dort, C.A.M. Hoefs, E.P. Magré, A.J. Schöpf, K. Yntema, Poly-p-phenylene oxide European Polymer Journal. ,vol. 4, pp. 275- 287 ,(1968) , 10.1016/0014-3057(68)90041-4
Samiran Mahapatra, Jason A. Halfen, Elizabeth C. Wilkinson, Lawrence Que, William B. Tolman, Modeling Copper-Dioxygen Reactivity in Proteins: Aliphatic C-H Bond Activation by a New Dicopper(II)-Peroxo Complex Journal of the American Chemical Society. ,vol. 116, pp. 9785- 9786 ,(1994) , 10.1021/JA00100A068
Allan S. Hay, The SPE international award address?1975 polymerization by oxidative coupling?an historical review Polymer Engineering and Science. ,vol. 16, pp. 1- 10 ,(1976) , 10.1002/PEN.760160102
Samiran Mahapatra, Jason A. Halfen, Elizabeth C. Wilkinson, Gaofeng Pan, Christopher J. Cramer, Lawrence Jr. Que, William B. Tolman, A New Intermediate in Copper Dioxygen Chemistry: Breaking the O-O Bond To Form a {Cu2(.mu.-O)2}2+ Core Journal of the American Chemical Society. ,vol. 117, pp. 8865- 8866 ,(1995) , 10.1021/JA00139A026
Hiroshi Uyama, Hideharu Kurioka, Isao Kaneko, Shiro Kobayashi, Synthesis of a New Family of Phenol Resin by Enzymatic Oxidative Polymerization Chemistry Letters. ,vol. 23, pp. 423- 426 ,(1994) , 10.1246/CL.1994.423
Nobumasa Kitajima, Kiyoshi Fujisawa, Chisato Fujimoto, Yoshihiko Morooka, Shinji Hashimoto, Teizo Kitagawa, Koshiro Toriumi, Kazuyuki Tatsumi, Akira Nakamura, A new model for dioxygen binding in hemocyanin. Synthesis, characterization, and molecular structure of the .mu.-.eta.2:.eta.2 peroxo dinuclear copper(II) complexes, [Cu(HB(3,5-R2pz)3)]2(O2) (R = isopropyl and Ph) Journal of the American Chemical Society. ,vol. 114, pp. 1277- 1291 ,(1992) , 10.1021/JA00030A025