Abstract
Cationic ring-opening copolymerizations of O-Permethylcyclodextrins (MeCDs) with tetrahydrofuran (THF) were studied. In THF that is the comonomer as well as the solvent, MeOTf as the initiator produced the copolymer consisting of tri-O-methylglucopyranose and tetramethylene ether units, while Et3O+PF6− mainly conducted the homopolymerization of THF. The addition of CH2Cl2 as the cosolvent favorably promoted the polymerization of MeCDs, producing the copolymer from both initiators. Interestingly, the initiator system of HI/I2 was found to chemoselectively polymerize MeCDs even in THF.
Similar content being viewed by others
Article PDF
References
M. Suzuki, O. Numata, and T. Shimazaki, Macromol. Rapid Commun., 22, 1354 (2001).
M. Suzuki and T. Shimazaki, Org. Biomol. Chem., 1, 604 (2003).
M. Suzuki, O. Numata, and T. Shimazaki, Macromol. Symp., 215, 255 (2004).
R. Adden, A. Bösch, and P. Mischnick, Macromol. Chem. Phys., 205, 2072 (2004).
A. Bösch, M. Nimtz, and P. Mischnick, Cellulose, 13, 493 (2006).
A. Bösch and P. Mischnick, Biomacromolecules, 8, 2311 (2007).
J. Thiem and W. A. Strietholt, Macromol. Chem. Phys., 196, 1487 (1995) and references cited therein.
G. Schomburg, A. Deege, H. Hinrichs, E. Hübinger, and H. Husmann, J. High Resolut. Chromatogr., 15, 579 (1992).
A. Kanazawa, S. Okumura, and M. Suzuki, Org. Biomol. Chem., 3, 1746 (2005). The procedure used therein for the hydrolysis of the O-methylated glucan was employed.
G. N. Bollenback, Meth. Carbohydr. Chem., 2, 326 (1963). The procedure used therein for the formation of methyl glucoside was applied.
The O-methylation procedure for CD mentioned in ref 8 was employed.
S. Kobayashi, H. Uyama, M. Ogaki, T. Yoshida, and T. Saegusa, Macromolecures, 22, 4412 (1989).
The detailed mechanism and discussion of the acetal exchange reaction are available in refs 2 and 3.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Suzuki, M., Shimazaki, T. Cationic Ring-Opening Copolymerization of O-Permethylcyclodextrin with Tetrahydrofuran. Polym J 40, 640–644 (2008). https://doi.org/10.1295/polymj.PJ2008043
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1295/polymj.PJ2008043