Abstract
A new acyl-group transfer polymerization of thiiranes using carboxylic acid derivatives and quaternary onium salts was investigated. 3-Phenoxypropylene sulfide (PPS) was polymerized efficiently by S-phenyl thioacetate in the presence of tetrabutylammonium chloride, bromide, or tetrabutylphosphonium chloride to give the corresponding polysulfide with a S-acetyl group at the polymer terminal. The polymerization of 3-butoxypropylene sulfide (BPS) and cyclohexene sulfide (CHS) also proceeded under the similar conditions to afford the corresponding polymers. It was found from the polymer structures and results of post-polymerization that the polymerization proceeded transferring an acyl group in each propagating step. It was demonstrated that the acyl-group transfer polymerization has living nature. Furthermore, di- and tri-block copolymers of a variety of thiiranes were successfully synthesized by the present acyl-group transfer polymerization.
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O. W. Webster, W. R. Hertler, D. Y. Sogar, W. B. Farnham, and T. V. RajanBaub, J. Am. Chem. Soc., 105, 5703 (1983).
As a review: A. H. Muller, Makromol. Chem. Symp., 32, 87 (1990).
H. Catalgil, N. Vyanik, and C. Erbil, Polymer, 33, 655 (1992).
K. G. Bannerjee and T. E. Hogen-Esch, Macromolecules, 26, 926 (1993).
R. P. Quirk and C. P. Bindinen, Polym. Bull., 22, 63 (1989).
R. P. Quirk and J. Rem, Macromolecules, 25, 6612 (1992).
D. Y. Sogah and O. W. Webster, Macromolecules, 19, 1775 (1986).
T. Hirabayashi, T. Itoh, and K. Yokota, Polym. J., 20, 1041 (1988).
H. Sumi, K. Haraguchi, Y. Inai, T. Hirabayashi, and K. Yokota, Polym. J., 26, 1262 (1994).
T. Nishikubo and A. Kameyama, Prog. Polym. Sci., 18, 963 (1993).
A. Kameyama, M. Kiyota, and T. Nishikubo, Tetrahedron Lett., 35, 4571 (1994).
A. Kameyama, S. Watanabe, E. Kobayashi, and T. Nishikubo, Macromolecules, 25, 2307 (1992).
A. Kameyama, Y. Yamamoto, and T. Nishikubo, J. Polym. Sci., Part A: Polym. Chem., 31, 1639 (1993).
A. Kameyama, K. Shimotsuma, and T. Nishikubo, Macromol. Rapid Commun., 15, 335 (1994).
R. Ketcham and V. P. Shah, J. Org. Chem., 28, 229 (1963).
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Kameyama, A., Shimotsuma, K. & Nishikubo, T. New Acyl-Group Transfer Polymerization of Thiiranes Using Carboxylic Acid Derivatives and Quaternary Onium Salts. Polym J 28, 68–75 (1996). https://doi.org/10.1295/polymj.28.68
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DOI: https://doi.org/10.1295/polymj.28.68
