Abstract
Regioselective addition reaction of phenyl glycidyl ether with S-phenyl thioacetate was carried out using the complex catalyst of the polymer-supported crown ether with potassium phenoxide in aprotic polar solvents, and the corresponding adduct 2-acetoxy-3-(phenylthio)-propyl phenyl ether was obtained in high yield with small amounts of by-product 2-hydroxy-3-(phenylthio)-propyl phenyl ether. Furthermore, it was found that the rate of the reaction and yield of the adduct were affected by the degree of introduction of the crown ether residue, the degree of crosslinking of the polystyrene bead, the reaction solvent, and the kind of potassium salt.
Similar content being viewed by others
Login or create a free account to read this content
Gain free access to this article, as well as selected content from this journal and more on nature.com
or
References
E. Blasius, K. P. Janzen, M. Keller, H. Lander, T. Nguyen-Tien, and G. Scholten, Talanta, 27, 107 (1980).
E. Blasius, K. P. Janzen, W. Adrian, W. Klein, H. Klotz, H. Luxemburger, E. Mernke, V. B. Nguyen, T. Nguyen-Tien, R. Rausch, J. Stockemer, and A. Toussaint, Talanta, 27, 127 (1980).
M. Igawa, K. Saito, J. Tsukamoto, and M. Tanaka, Anal. Chem., 53, 1942 (1981).
M. Nakajima, K. Kimura, and T. Shono, Anal. Chem., 55, 463 (1983).
F. Montanari and P. Tundo, J. Org. Chem., 46, 2125 (1981).
P. Tundo and P. Venturello, J. Am. Chem. Soc., 103, 856 (1981).
K. Fukunishi, B. Czech, and S. L. Regen, J. Org. Chem., 46, 1218 (1981).
M. Tomoi, N. Yanai, S. Shiiki, and H. Kakiuchi, J. Polym. Sci., Polym. Chem. Ed., 22, 911 (1984).
K. Zhang, G. S. Kumar, and D. C. Neckers, J. Polym. Sci., Polym. Chem. Ed., 23, 1293 (1985).
T. Nishikubo, T. Iizawa, and S. Saita, E. Takahashi, and F. Nono, Macromolecules, 18, 2131 (1985).
T. Iizawa, A. Goto, and T. Nishikubo, Bull. Chem. Soc., Jpn., 62, 597 (1989).
T. Nishikubo and K. Sato, Chem. Lett., 697 (1991).
T. Nishikubo, T. Iizawa, M. Shimojyo, T. Kato, and A. Shiina, J. Org. Chem., 55, 2536 (1990).
T. Nishikubo, T. Kato, Y. Sugimoto, M. Tomoi and S. Ishigaki, Macromolecules, 23, 3406 (1990).
T. Nishikubo, T. Kato, M. Tomoi, and S. Ishigaki, Polym. J., 21, 669 (1989).
M. Tomoi, N. Yamai, S. Shiiki, and H. Kakiuchi, J. Polym. Sci., Polym. Chem. Ed., 22, 911 (1984).
K. Miyaki and S. Yamagishi, J. Pharam. Soc., Jpn., 76, 436 (1956).
T. Nishikubo, Y. Sugimoto, and K. Sato, Nippon Kagaku Kaishi, in press.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Nishikubo, T., Sugimoto, Y. & Tomoi, M. New Catalytic Activity of Insoluble Polymer-Supported Crown Ethers for Addition Reaction of Oxirane with Active Ester. Polym J 23, 1467–1472 (1991). https://doi.org/10.1295/polymj.23.1467
Issue date:
DOI: https://doi.org/10.1295/polymj.23.1467
