Abstract
Polystyrenes bearing tricyclohexylstannyl moieties with different stereoregularities, molecular weights, and chemical composition have been prepared and characterized through two synthetic routes. The suitability of the products obtained to be used as intermediate derivatives in the synthesis of the corresponding organotin trichlorides, precursors to organic–inorganic hybrid materials, has been investigated.
Similar content being viewed by others
REFERENCES
W. P. Neumann, The Organic Chemistry of Tin (Wiley, London, 1967). R. C. Poller, The Chemistry of Organotin Compounds (Logos, London, 1970). G. P. Van der Kelen, E. V. Van der Berghe, and L. Verdonck, in Organotin Compounds, A. K. Sawyer, ed. (Dekker, New York, 1971), p. 81. A. G. Davies and P. J. Smith, in Comprehensive Organometallic Chemistry, G. Wilkinson, F. G. A. Stone, and E. W. Abel, eds. (Pergamon Press, Oxford, 1982), p. 591. A. Davies, in Comprehensive Organometallic Chemistry, 2nd ed., G. Wilkinson, F. G. A. Stone, and E. W. Abel, eds. (Pergamon Press, New York, 1995), p. 217.
C. J. Evans and S. Karpel, J. Organomet. Chem. Lib. 16, 7 (1985).
H. Schumann and I. Schumann, in Gmelin Handbook of Inorganic Chemistry, H. Bitterer, ed. (Springer-Verlag, Berlin, 1979), p. 210.
E. Fouquet, B. Jousseaume, B. Maillard, and M. Pereyre, J. Organomet. Chem. 453, C1 (1993).
B. Jousseaume, M. Lahcini, M.-C. Rascle, C. Sanchez, and F. Ribot, Organometallics 14, 685 (1995).
Y. Yamamoto, S. Hatsuya, and J. Yamada, J. Org. Chem. 55, 3118 (1990).
I. Ryu, S. Murai, and N. Sonoda, J. Org. Chem. 51, 2389 (1986). H. Nakahira, I. Ryu, M. Ikebe, Y. Oku, A. Ogawa, N. Kambe, N. Sonoda, and S. Murai, J. Org. Chem. 57, 17 (1992). E. Nakamura, J. I. Shimada, and I. Kuwajima, Organometallics 4, 641 (1985). H. Nakahira, I. Ryu, A. Ogawa, N. Kambe, and N. Sonoda, Organometallics 9, 277 (1990).
B. Jousseaume, M. Lahcini, E. Fouquet, and B. Barbe, J. Org. Chem. 59, 8292 (1994).
A. I. Roshchin, N. A. Bumagin, and I. P. Beletskaya, Tetrahedron Lett. 125 (1995). R. Rai, K. B. Aubrecht, and D. B. Collum, Tetrahedron Lett. 3111 (1995).
E. Fouquet, A. Gabriel, B. Maillard, and M Pereyre, Tetrahedron Lett. 7749 (1993). E. Fouquet, A. Gabriel, B. Maillard, and M. Pereyre, Bull. Soc. Chim. Fr. 132, 590 (1995).
Y. Yamamoto, S. Hatsuya, and J. Yamada, J. Org. Chem. 55, 3118 (1990).
H. Schumann and I. Schumann, in Gmelin Handbook of Inorganic Chemistry of Tin, U. Krüerke, ed. (Springer-Verlag, Berlin, 1989), p. 12.
P. Jaumier, B. Jousseaume, M. Lahcini, F. Ribot, and C. Sanchez, J. Chem. Soc. Chem. Commun. 369 (1998).
F. Ribot, F. Banse, C. Sanchez, M. Lahcini, and B. Jousseaume, J. Sol-Gel Sci. Tech. 8, 529 (1997).
H. H. Wuang, B. Orler, and G. L. Wilkes, Macromolecules 20, 1322 (1987). B. M. Novak, Adv. Mater. 5, 422 (1993). H. Schmidt, and B. Seiferling, Mater. Res. Soc. Symp. Proc. 73, 739 (1986). C. Sanchez and F. Ribot, New J. Chem. 18, 1007 (1994). U. Schubert, N. Hüsing, and A. Lorenz, Chem. Mater. 7, 2010 (1995). D. A. Loy and K. J. Shea, Chem. Rev. 95, 1431 (1995).
M. Gerlach, F. Jordens, H. Kunh, W. P. Neumann, and M. Peterseim, J. Org. Chem. 56, 5971 (1991). W. P. Neumann and M. Peterseim, React. Polym. 20, 189 (1993). G. Dumartin, G. Ruel, J. Kharboutli, B. Delmond, M. F. Connil, B. Jousseaume, and M. Pereyre, Synlett 952 (1994). G. Ruel, G. Dumartin, B. Delmond, B. Lalere, O. F. X. Donard, and M. Pereyre, Appl. Organometal. Chem. 9, 591 (1995).
K. N. Somasekharan and R. V. Subramanian, in Controlled Release of Bioactive Materials, R. W. Baker, ed. (Academic Press, New York, 1980).
Z. M. O. Rzaev, in Topics in Current Chemistry, F. L. Boschke, ed. (Springer-Verlag, Berlin, 1982), Vol. 104, p. 107.
D. E. Bergbreiter, J. R. Blanton, R. Chandran, M. D. Hein, K.-J. Huang, D. R. Treadwell, and S. A. Walker, J. Polym. Sci. A Polym. Chem. 27, 4205 (1989).
D. D. Perrin, W. L. F. Armarego, and D. R. Perrin, Purification of Laboratory Chemicals (Pergamon Press, Oxford, 1966).
J. C. Pommier, M. Pereyre, and J. Valade, C. R. Acad. Sci. 260, 6397 (1965).
K. Pielichowski, A. Puszynski, and J. Pielichowski, Polym. J. 26, 822 (1994).
M. M. Koton and L. F. Dokukina, Zh. Obshch. Khim. 34, 1757 (1964); Chem. Abstr. 61, 8331g (1964).
J. G. Noltes, H. A. Budding, and G. J. M. Van der Kerk, Recueil 79, 1076 (1960).
J. R. Leebrick and H. E. Ramsden, J. Org. Chem. 23, 935 (1958).
M. Szwarc, M. Levy, and R. Milkovich, J. Am. Chem. Soc. 78, 2656 (1956).
Y. V. Kissin, Isospecific Polymerization of Olefins (Springer-Verlag, New York, 1985), Chap. IV.
N. Ishihara, T. Seimiya, M. Kuramoto, and M. Uoi, Macromolecules 19, 2464 (1986).
H. Sinn, W. Kaminsky, H.-J. Volmer, and R. Woldt, Angew. Chem. Int. Ed. Engl. 19, 390 (1980).
M. Zeldin and J. J. Lin, J. Polym. Sci. Polym. Chem. Ed. 23, 2333 (1985).
F. A. Bovey, in Comprehensive Polymer Science, G. Allen, ed. (Pergamon Press, Oxford, 1989), Vol. 1, p. 339.
M. Camps, J. P. Montheard, F. Benrokia, J. M. Camps, and Q. T. Pham, Eur. Polym. J. 26, 53 (1990).
F. C. Leavitt and L. U. Matternas, J. Polym. Sci. 145, 259 (1960). D. Braun, Makromol. Chem. 30, 85 (1959). B. Houel, C. R. Acad. Sci. 2209 (1960). N. L. Brockmann and A. E. Eisenberg, J. Polym. Sci. Polym. Chem. 21, 3563 (1983).
S. S. Al-Diab, J. Chem. Res. (S), 90 (1987).
D. E. Bergbreiter and S. A. Walker, J. Org. Chem. 54, 5138 (1989).
S. S. Al-Diab, H.-K. Suh, J. E. Mark, and H. Zimmer, J Polym. Sci. A Polym. Chem. 28, 299 (1990).
M. M. Koton and L. F. Dokukina, Dokl. Akad. Nauk SSSR 152, 1357 (1963); Chem. Abstr. 60, 3099c (1964).
F. Ignatious, Y. Delaviz, I. Cabasso, and J. Smid, Macromol. Chem. Macromol. Symp. 60, 247 (1992).
N. Yamazaki, S. Nakahama, A. Hirao, J. Goto, Y. Shiraishi, F. Martinez, and H. M. Phung, J. Macromol. Sci. Chem. A16, 1129 (1981).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Angiolini, L., Caretti, D., Carlini, C. et al. Synthesis of Polystyrene-Bound Organotin Derivatives as Intermediates for the Production of Hybrid Materials. Journal of Inorganic and Organometallic Polymers 8, 47–65 (1998). https://doi.org/10.1023/A:1021674019909
Issue Date:
DOI: https://doi.org/10.1023/A:1021674019909