Abstract
Head-to-head poly(2-vinylnaphthalene) was prepared in five steps from 2-naphthylacetic acid. The methyl ester was brominated with N-bromosuccinimide and 2(2-naphthyl)2-bromoacetate treated with a copper/zinc couple, which gave dimethyl 2,3-di(2-naphthyl)succinate in moderate yield. This compound was reduced with lithium aluminum hydride to 2,3-di(2-naphthyl)butanediol-1,4 and the hydroxyl groups replaced by bromine. 2,3-Di(2-naphthyl)-1,4-dibromobutane was subjected to the Yamamoto coupling polycondensation; head-to-head poly(2-vinylnaphthalene) was obtained in relatively low yield and of modest molecular weight.
Similar content being viewed by others
Article PDF
References
O. Vogl, M. Malanga, and W. Berger, “Contemporary Topics in Polymer Science,” Vol. 4, W. J. Bailey and T. Tsuruta, Ed., Plenum Press, New York, London, 1983, p 35.
O. Vogl, J. Macromol. Sci., Chem., A21, 1725 (1984).
O. Vogl and S. Grossman, Encyclopedia of Polymer Science and Technology, 7 (1986).
H. Kawaguchi, Y. Sumida, J. Muggee, and O. Vogl, Polymer, 23, 1805 (1982).
S. Grossman, A. Stolarczyk, and O, Vogl, Monatsh. Chem., 112, 1279 (1981).
H. Inoue, M. Helbig, and O. Vogl, Macromolecules, 10, 1331 (1977).
L. S. Corley, H. Inoue, M. Helbig, and O. Vogl, Macromol. Synth., 9, 31 (1985).
C. Starzielle, H. Benoit, and O. Vogl, Eur. Polym. J., 14, 331 (1978).
E. Marchal, H. Benoit, and O. Vogl, J. Polym. Sci., Polym. Phys. Ed., 16, 949 (1978).
F. Laupretre, L. Monnerie, and O. Vogl, Eur. Polym. J., 14, 981 (1978).
G. Weill and O. Vogl, Polym. Bull., 1, 181 (1978).
J. M. Torkelson, S. Lipsky, and M. Tirrell, Macromolecules, 14, 1601 (1981).
W. E. Lindsell, F. C. Robertson, and I. Soutar, Eur. Polym. J., 17, 203 (1981).
L. P. Hu, M. Nanasawa, and O. Vogl, Polym. Prepr., ACS, Div. Polym. Chem., 27(1), 377 (1986).
M. Nanasawa, d L. P. Hu, and O. Vogl, Polymer, in press.
N. Acton and E. Berliner, J. Am. Chem. Soc., 86, 3312 (1964).
F. H. Jardine, Adv. Inorg. Chem. Radiochem., 17, 115 (1975).
T. Yamato, T. Taguchi, K. Sanechika, Y. Hayashi, and A. Yamamoto, Macromolecules, 16, 1555 (1983).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Nanasawa, M., Hu, L. & Vogl, O. Head-to-Head Polymers XXXV. Head-to-Head Poly(2-vinylnaphthalene). Polym J 18, 681–687 (1986). https://doi.org/10.1295/polymj.18.681
Issue Date:
DOI: https://doi.org/10.1295/polymj.18.681
Keywords
This article is cited by
-
Maleic acid?2-vinylnaphthalene copolymer in aqueous solution: investigation of the dissociation and fluorescence quenching
Journal of Polymer Research (2011)