Summary
Addition of iodine monochloride to E-1,4-poly(2-triethylsilyl-1,3-butadiene) (I) followed by treatment with potassium fluoride dihydrate yields a copolymer comprised of E and Z-1,4-(2-iodo-1,3-butadiene) (E and Z-II) units and 2-1,4-(2-chloro-1,3-butadiene) (Z-III) units. The mechanism of this reaction is discussed. The product copolymer has been characterized by1H and13C NMR, IR, UV, GPC, TGA and elemental analysis.
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References
Fettes, E.M., ed., “Chemical Reactions of Polymers,” Interscience Publishers, New York (1964).
Carraher, C.E., Jr., Moore, J.A., eds., “Modification of Polymers,” Plenum Press, New York (1983).
Mathias, L.J., Carraher, C.E., Jr., eds., “Crown Ethers and Phase Transfer Catalysis in Polymer Science,” Plenum Press, New York (1984).
Benham, J.L, Kinstele, J.F., eds., “Chemical Reactions on Polymers,” ACS Symposium Series 364, Amer. Chem. Soc., Washington, D.C., (1988).
Weber, W.P., “Silicon Reagents for Organic Synthesis,” Springer-Verlag, Berlin, (1983) p 79–92.
Colvin, E.W., “Silicon in Organic Synthesis, London, Butterworth, 1981.
Okano, Y. Masuda, T., Higashimura, T., J. Polymer Sci.,22, 1603 (1984).
Zeigler, J.M., Polymer Preprints,25, 223 (184).
Voronkov, M.G., Pukhnarevich, V.B., Sushchinskaya, S.P., Annenkova, V.Z., Annenkova, V.M., Andreeva, N.J., J. Polymer Sci. Polymer Chem. Ed.,18, 53 (1980).
Miller, R.B., McGarvey, G., Synth. Commun.,8, 291 (1978).
Huynh, C., Linstrumelle, G., Tetrahedron Lett.,1979, 1073.
Jiang, W., Weber, W.P., Polymer Bulletin,20, 15 (1988).
Ding, Y.X., Weber, W.P., Macromolecules,21 530 (1988).
Noyes, R.M., Dichison, R.G., Schomaker, V., J. Am. Chem. Soc.,67, 1319 (1945).
E. Eliel, “Stereochemistry of Carbon Compounds,” McGraw Hill Book Co. Inc., New York, 1962, p. 341–346.
Neuman, R.C. Jr., Holmes, G.D., J. Org. Chem.,33, 4317 (1968).
Pham, Q.T., Petiaud, R., Waton, H., “Proton and Carbon NMR Spectra of Polymers,” J. Wiley & Sons, New York, 1983. Vol. 1, p 88, Vol. 2, p 294.
Ebdon, J.R., Polymer,19, 1232 (1978).
Stothers, J. B., Carbon-13 NMR Spectroscopy, Academic Press, New York, 1972, p. 183.
Stille, J.K., Simpson, J.H., J. Am. Chem. Soc.,109, 2138 (1987).
Ungnade, H.E., Hill, M.E., Kamlet, M.J., “Organic Electronic Spectral Data, Inc.,” Interscience, New York, Vol. 1, 1957.