Abstract
Three chiral diols, 1,2:5,6-di-O-isopropylidene-, 1,2:4,6-di-O-isopropylidene-, and 1,2:4,5-di-O-isopropylidene-D-mannitol (a, b, and c, respectively) were used as template for chirality induction in the cyclocopolymerizations of bis(4-vinylbenzoate) monomers (1a, 1b, and 1c) with styrene. The chirality of polymers 3a and 3b was opposite to that of monomers 1a and 1b on their CD spectra. In contrast, the chirality of polymer 3c was the same as that of monomer 1c. The efficiency of template on the chirality induction decreased in the order of b>a>c. The efficiency is lower for template b than the corresponding acyclic template e, though being higher for templates a and c than the acyclic templates d and i, respectively. These characters of the mannitol templates were discussed on the basis of the most suitable conformer in the monomers.
Similar content being viewed by others
Article PDF
References
Y. Okamoto and T. Nakano, Chem. Rev., 94, 349 (1994).
K. Yokota, O. Haba, T. Satoh, and T. Kakuchi, Macromol. Chem. Phys., 196, 2383 (1995).
G. Wulff, Angew. Chem. Int. Ed. Engl., 28, 21 (1989).
G. Wulff, R. Kemmerer, and B. Vogt, J. Am. Chem. Soc., 109, 7449 (1987).
T. Kakuchi, O. Haba, N. Fukui, T, Uesaka, M. Obata, and K. Yokota, Polymer, 37, 5703 (1996).
T. Kakuchi, O. Haba, E. Hamaya, T. Naka, T. Uesaka, and K. Yokota, Macromolecules, 29, 3807 (1996).
T. Kakuchi, O. Haba, N. Fukui, and K. Yokota, Macromolecules, 28, 5941 (1995).
K. Nakanishi, N. Berova, and R. W. Woody, “Circular Dichroism–Principles and Applications,” VCH Publishers Inc., New York, N.Y., 1994, p 361.
N. Harada and K. Nakanishi, “Circular Dichroic Spectroscopy–Exciton Coupling in Organic Stereochemistry,” Mill Valley, CA, and Oxford University Press, Oxford, 1983.
K. Yokota, T. Kakuchi, T. Uesaka, and M. Obata, Acta Polymerica, 48, 459 (1997).
T. Kakuchi, T. Uesaka, M. Obata, and K. Yokota, Kobunshi Ronbunshu, 54, 684 (1997).
M. Obata, T. Uesaka, K. Yokota, and T. Kakuchi, Macromolecules, 31, 4403 (1998).
T. Uesaka, E. Hamaya, O. Haba, T. Kakuchi, and K. Yokota, Enantiomer, 2, 215 (1997).
J. Kuszmann, É. Tomori, and P. Dvortsák, Carbohydr. Res., 132, 178 (1984).
A. Hirao, Y. Ishino, and S. Nakahama, Macromolecules, 21, 561 (1988).
T. H. Boer and H. J. Backer, Org. Syn. Coll., IV, 250 (1963).
F. Tüdös, T. Kelen, T. Földes-Berezsnich, and B. Turcsányi, J. Macromol. Sci., Chem., A10, 1513 (1976).
The AM1 calculations were carried out using the Mac Spartan Plus (Wavefunction, Inc.) program.
K. Ito and Y. Yamashita, J. Polym. Sci., Part A: Polym. Chem., 3, 2165 (1965).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Uesaka, T., Sugiura, Y., Obata, M. et al. Chirality Induction in Cyclopolymerization X. Structural Effect of Three D-Mannitol Templates in the Cyclocopolymerization of Bis(4-vinylbenzoate) with Styrene. Polym J 31, 342–347 (1999). https://doi.org/10.1295/polymj.31.342
Issue Date:
DOI: https://doi.org/10.1295/polymj.31.342