Abstract
Polymerizability of isomerically trimethylsilyl and pentamethyldisiloxanyl substituted styrenes was studied. In the polymerization, o-substituted isomers gave low molecular weight polymer in low yield. Chain transfer constant to the o-trimethylsilyl substituted monomer was estimated to be quite large as a styrene type monomer. In NMR spectrum, α-vinyl proton of o-isomers shifted to the lower field compared with that of m- or p-isomers, and 9% of nuclear Overhauser enhancement (NOE) was observed for α-vinyl proton of o-trimethylsilylstyrene under irradiation on silylmethyl proton. The characteristic polymerization behavior of the o-isomers is discussed.
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Y. Kawakami, T. Aoki, H. Hisada, Y. Yamamura, and Y. Yamashita, Polym. Commun., 26, 133 (1985).
Y. Kawakami, H. Karasawa, T. Aoki, Y. Yamamura, H. Hisada, and Y. Yamashita, Polym. J., 17, 1159 (1985).
Y. Kawakami, H. Karasawa, H. Kamiya, T. Aoki, and Y. Yamashita, Polym. J., 18, 237 (1986).
Y. Kawakami, T. Sugisaka, and Y. Yamashita, Polym. J., 20, 685 (1988).
Y. Kawakami and T. Sugisaka, J. Membrane Sci., 50, 189 (1990).
W. Takagi, I. Inoue, Y. Yano, and T. Okonogi, Tetrahedron Lett., 2587 (1974).
G. M. Pogosyan, L. M. Akopyan, E. V. Vanyan, and S. G. Matsoyan, Vysokomol. Soedin., Ser. B, 13, 242 (1971).
J. Brandrup and E. H. Immergut, “Polymer Handbook,” third ed, Wiley Interscience, New York, N.Y., 1989.
G. Odian, “Principles of Polymerization,” John Wiley & Sons, New York, N.Y., 1981, p 250.
L. M. Jackman and S. Sternhell, “Application of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry,” Pergamon Press, New York, N.Y., 1969, p 71.
E. Breitmaier and W. Voelter, “Carbon-13 NMR Spectroscopy,” VCH Publishers, Weinheim, Germany, 1987, p 115.
E. Colvin, “Silicon in Organic Synthesis,” Butterworth and Co., London, 1981, p 10.
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Kawakami, Y., Cairo, R. Polymerizability of Isomerically Trimethylsilyl Substituted Styrenes. Polym J 23, 285–296 (1991). https://doi.org/10.1295/polymj.23.285
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DOI: https://doi.org/10.1295/polymj.23.285