Share This Article:

Oxidative coupling polymerization of p-alkoxyphenols with Mn(acac)2-ethylenediamine catalysts

Abstract Full-Text HTML Download Download as PDF (Size:381KB) PP. 803-808
DOI: 10.4236/ns.2010.28101    6,204 Downloads   12,760 Views   Citations

ABSTRACT

The oxidative coupling polymerization of p alkoxyphenols with Mn(acac)2ethylenediamine catalysts was carried out. The polymerization of pmethoxyphenol with the manganese(II) acetylacetonate [Mn(acac)2]N,N’diethylethylene diamine catalyst in CH2Cl2 at room temperature under an O2 atmosphere afforded a polymer, which mainly consists of the mphenylene unit, whereas the polymer obtained with Mn(acac)2 was rich in the oxyphenylene structure. The polymer yield and regioselectivity were significantly affected by the monomer and catalyst structures. The former catalyst system was also used for the coupling reaction of 2methoxy 4methylphenol. The corresponding carboncar bon coupling product was isolated with a regioselectivity of 95%.

Conflicts of Interest

The authors declare no conflicts of interest.

Cite this paper

Murakami, S. , Akutsu, Y. , Habaue, S. , Haba, O. and Higashimura, H. (2010) Oxidative coupling polymerization of p-alkoxyphenols with Mn(acac)2-ethylenediamine catalysts. Natural Science, 2, 803-808. doi: 10.4236/ns.2010.28101.

References

[1] Xu, M.H., Lin, A.M. and Pu, L. (2001) Construction of an orthophenol polymer. Tetrahedron Letters, 42(36), 62356238.
[2] Katagiri, H., Miyagawa, T., Furusho, Y. and Yashima, E. (2006) Synthesis and optical resolution of a double helicate consisting of ortholinked hexaphenol strands bridged by spiroborates. Angewandte Chemie Interna tional Edition in English, 45(11), 17411744.
[3] Ueda, M. and Ichikawa, F. (1990) Synthesis of aromatic poly (ether ketone)s by nickelcatalyzed coupling polymerization of aromatic dichlorides. Macromolecules, 23(4), 926930.
[4] Colon, I. and Kwiatkoeski, G.T. (1990) High molecular weight aromatic polymers by nickel coupling of aryl polychlorides. Journal of Polymer Science: Part A: Polymer Chemistry, 28(2), 367383.
[5] Hay, A.S., Blanchard, H.S., Endres, G.F. and Eustance, J.W. (1959) Polymerization by oxidative coupling. Journal of American Chemical Society, 81(23), 6335 6336.
[6] Hay, A.S. (1998) Polymerization by oxidative coupling: Discovery and commercialization of PPO? and Noryl? resins. Journal of Polymer Science: Part A: Polymer Chemistry, 36(4), 505517.
[7] Kobayashi, S. and Higashimura, H. (2003) Oxidative polymerization of phenols revisited. Progress in Poly mer Science, 28(6), 10151048.
[8] Wang, P., Martin, B.D., Parida, S., Rethwisch, D.G. and Dordick, J.S. (1995) Multienzymic synthesis of poly (hydroquinone) for use as a redox polymer. Journal of American Chemical Society, 117(51), 1288512886.
[9] Reihmann, M.H. and Ritter, H. (2000) Enzymatically catalyzed synthesis of photocrosslinkable oligophenols. Macromolecular Chemistry and Physics, 201(14), 1593 1597.
[10] Fukuoka, T., Uyama, H. and Kobayashi, S. (2004) Effect of phenolic monomer structure of precursor polymers in oxidative coupling of enzymatically synthesized poly phenols. Macromolecules, 37(16), 59115915.
[11] Etori, H., Kanbara, T. and Yamamoto, T. (1994) New type of―conjugated polymers constituted of quinone units in the main chain. Chemistry Letters, 23(3), 461 464.
[12] Tonami, H., Uyama, H., Kobayashi, S. and Kubota, M. (1999) Peroxidasecatalyzed oxidative polymerization of msubstituted phenol derivatives. Macromolecular Che mistry and Physics, 200(10), 23652371.
[13] Oguchi, T., Tawaki, S., Uyama, H. and Kobayashi, S. (1999) Soluble polyphenol. Macromolecular Rapid Com munications, 20(7), 401413.
[14] Kim, Y.J., Uyama, H. and Kobayashi, S. (2003) Regioselective synthesis of poly(phenylene) as a complex with poly(ethylene glycol) by template poly merization of phenol in water. Macromolecules, 36(14), 50585060.
[15] Higashimura, H., Fujisawa, K., Kubota, M. and Kobayashi. S. (2005) “Radicalcontrolled” oxidative polymerization of phenol: Comparison with that of 4phenoxyphenol. Journal of Polymer Science: Part A: Polymer Chemistry, 43(9), 19551962.
[16] Shibasaki, Y., Suzuki, Y. and Ueda, M. (2007) Copper catalyzed regiocontrolled oxidative coupling polyme rization of 2,5dimethylphenol. Macromolecules, 40(15), 53225325.
[17] Habaue, S., Ohnuma, M., Mizoe, M. and Temma, T. (2005) Oxidative coupling polymerization of silicon tethered palkoxyphenol derivatives with CuCl(OH)N,N, N’,N’Tetramethylethylenediamine Catalyst. Polymer Jour nal, 37(8), 625628.
[18] Habaue, S., Murakami, S. and Higashimura, H. (2005) New asymmetric vanadium catalyst for highly selective oxidative coupling polymerization. Journal of Polymer Science: Part A: Polymer Chemistry, 43(23), 58725878.
[19] Murakami, S., Habaue, S. and Higashimura, H. (2007) Novel vanadium catalyst system with tartaric acid salts for highly selective asymmetric oxidative coupling poly merization. Polymer, 48(22), 65656570.
[20] Habaue, S., Aoyagi, H., Murakami, S. and Higashimura, H. (2007) Asymmetric oxidative coupling polymeri zation of dihydroxynaphthalene derivatives with cobalt Salen complexes. Polymer Bulletin, 59(3), 303310.
[21] Sun, Y., Fenster, M., Yu, A., Brerry, R.M. and Argyropoulos, D.S. (1999) The effect of metal ions on the reaction of hydrogen peroxide with kraft lignin model compounds. Canadian Journal of Chemistry, 77(56), 667675.
[22] Fabbri, D., Dettori, M.A., Delogu, G., Forn, I.A., Casalone, G., Palmieri, G., Pisano, M. and Rozzo, C. (2007) 2,2’Dihydroxy3,3’dimethoxy5,5’dimethyl6, 6’dibromo1,1’biphenyl: Preparation, resolution, structure and biological aActivity. Tetrahedron Asymmetry, 18(3), 414423.
[23] Alexakis, A., Polet, D., Rosset, S. and March, S. (2004) Biphenolbased phosphoramidite ligands for the en antioselective coppercatalyzed conjugate addition of diethylzinc. Journal of Organic Chemistry, 69(17), 5660 5667.

  
comments powered by Disqus

Copyright © 2019 by authors and Scientific Research Publishing Inc.

Creative Commons License

This work and the related PDF file are licensed under a Creative Commons Attribution 4.0 International License.