Synthesis of aromatic polyethers by scholl reaction. VIII. On the polymerizability of 1,5-bis(phenoxy)pentanes and 1,5-bis(phenylthio)pentane |
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Authors: | Virgil Percec James H. Wang Yoshi Oishi |
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Abstract: | The synthesis and the oxidative polymerization of 1,5-bis(phenoxy)pentane, 1,5-bis(phenoxy)pentane substituted with various electron-donating groups, and 1,5-bis(phenylthio)pentane is described. The polymers derived from methyl substituted 1,5-bis(phenoxy)pentane monomers contain diphenyl methane, 1,2-diphenylethane, and benzyl chloride structural units. The mechanism for the generation of these structural units is presented. It consists of the proton transfer reactions from the cation-radical propagating species and subsequent reactions of the resulting benzyl radicals. The polymerizability of monomers with 1,5-pentanedioxy group is lower than that of the monomers with diphenyl sulfone group. This dissimilarity was attributed to the difference between both the reactivity and the concentration of the cation-radical propagating species resulted from these two classes of monomers. |
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Keywords: | Scholl reaction cation-radical polymerization 1,5-bis(phenoxy)pentanes polymerization mechanism polymerizability of monomers proton transfer reactions |
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