Abstract
Optically active (R)-spiro[3.3]heptane-2,6-dicarboxylic acid was obtained by optical resolution with brucine. Its optical purity was confirmed by HPLC analysis on optically active stationary phase. The specific optical rotations of model compounds having one and two spiran units increased with increasing the number of spiran unit in sulfuric acid solution. On the contrary, the specific optical rotations showed opposite sign in organic solvents, such as N,N-dimethylformamide and N,N-dimethylacetamide, and the absolute values decreased with increasing the number of spiran unit. Polycondensation of (R)-spiro[3.3]heptane-2,6-dicarboxylic acid chloride and 3,3′-dimethoxybenzidine gave a polymer soluble in common organic polar solvents. This polymer showed a large positive Cotton effect.
Similar content being viewed by others
Log in 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
Y. Kawakami, K. Takeyama, K. Komuro, and O. Ooi, Macromolecules, 31, 551 (1998).
Y. Kawakami, T. Takahashi, Y. Yada, and I. Imae, Polym. J., 31, 1001 (1998).
Y. Li and Y. Kawakami, Macromolecules, 31, 5592 (1998).
Y. Li and Y. Kawakami, Macromolecules, 32, 548 (1999).
M. M. Green, C. Andreola, B. Munoz, M. P. Reidy, and K. Zero, J. Am. Chem. Soc., 110, 4063 (1988).
F. Millich and G. K. Baker, Macromolecules, 2, 122 (1969).
O. Vogl and G. D. Jaycox, Polymer, 28, 2179 (1987).
Y. Okamoto, K. Suzuki, K. Ohta, K. Hatada, and H. Yuki, J. Am. Chem. Soc., 81, 5475 (1979).
C. G. Overberger and D. W. Wang, J. Polym. Sci., Polym. Chem. Ed., 22, 1153 (1984).
R. C. Shulz and R. H. Jung, Makromol. Chem., 116, 190 (1968).
F. Kondo, M. Hidaka, S. Kakimi, H. Kimura, and M. Takeishi, ACS Polym. Prep., 38, 209 (1997).
F. Kondo, D. Takahashi, H. Kimura, and M. Takeishi, Polym. J., 30, 161 (1998).
L. Ma, Q. P. Hu, D. Vitharana, C. Wu, C. M. Kwan, and L. Pu, Macromolecules, 30, 204 (1997).
W. S. Huan, Q. S. Hu, X. F. Zheng, J. Anderson, and L. Pu, J. Am. Chem. Soc., 119, 4313 (1997).
M. R. Leonard and H. G. Charles, J. Org. Chem., 26, 54 (1961).
H. Tang, M. Baba, I. Imae, and Y. Kawakami, Polym. J., 31, 313 (1999).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Tang, H., Miura, H., Imae, I. et al. Optically Active Oligo- and Polyamides from Optically Active Spiro[3.3]heptane-2,6-dicarboxylic Acid. Polym J 31, 1041–1044 (1999). https://doi.org/10.1295/polymj.31.1041
Issue date:
DOI: https://doi.org/10.1295/polymj.31.1041
