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http://dx.doi.org/10.13160/ricns.2013.6.1.034

Disproportionation/Dehydrocoupling of Endocrine Disruptor, Tributyltin Hydride to Polystannanes Using Cp′2TiCl2/N-Selectride (Cp' = Cp' = C5H5, Cp; Me-C5H4, Me-Cp; Me5C5, Cp*) Catalyst  

Park, Jaeyoung (Department of Biotechnology, Chosun University)
Kim, Seongsim (Department of Biotechnology, Chosun University)
Lee, Beomgi (Department of Biotechnology, Chosun University)
Cheong, Hyeonsook (Department of Biotechnology, Chosun University)
Lee, Ki Bok (Department of Chemistry and Nanotechnology Research Center, Chonnam National University)
Woo, Hee-Gweon (Department of Chemistry and Nanotechnology Research Center, Chonnam National University)
Publication Information
Journal of Integrative Natural Science / v.6, no.1, 2013 , pp. 34-38 More about this Journal
Abstract
Tributyltin hydride ($n-Bu_3SnH$), an endocrine disruptor, was slowly polymerized by the group 4 ${Cp^{\prime}}_2TiCl_2/N$-selectride (Cp' = $C_5H_5$, Cp; $Me-C_5H_4$, Me-Cp; $Me_5C_5$, $Cp^*$) catalyst combination to give two phases of products: one is an insoluble cross-linked solid, polystannane in 3-25% yield as minor product via disproportionation/dehydrocoupling combination process, and the other is an oil, hexabutyldistannane in 65-90% yield as major product via simple dehydrocoupling process. Disproportionation/dehydrocoupling process first produced a low-molecular-weight oligostannane possessing partial backbone Sn-H bonds which then underwent an extensive cross-linking reaction of backbone Sn-H bonds, resulting in the formation of an insoluble polystannane. The disproportionation/dehydrocoupling of a tertiary hydrostannane mediated by early transition metallocene/inorganic hydride is quite unusual and applicable.
Keywords
Disproportionation; Dehydrocoupling; Polystannane; Titanocene; N-Selectride; Endocrine Disruptor;
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1 J. E. Mark, H. R.Allock, and R.West, "Inorganic polymers", Prentice Hall, New Jersey, 1992.
2 H. R. Allcock and F. W. Lampe, "Contemporary polymer chemistry", 2nd ed.; Prentice-Hall, Singapore, 1992.
3 S. Yajima, M. Omori, J. Hayashi, K. Okamura, T. Matsuzawa, and C. Liaw, "Simple synthesis of continuous SiC fibre with high tensile strength", Chem. Lett., pp. 551-554, 1976.
4 P. A. Bianconi and T. W. Weidman, "Poly(N-hexylsilyne): synthesis and properties of the first alkyl silicon [RSI]„ network polymer", J. Am. Chem. Soc., Vol. 110, pp. 2342-2344, 1988.   DOI
5 B. F. Griffing and R. Wet, "Contrast enhanced photoresists processing and modeling", Polym. Eng. Sci., Vol. 23, pp. 947-952, 1983.   DOI   ScienceOn
6 P. Trefonas III, J. R. Damewood Jr., R. West, and R. D. Miller, "Organosilane high polymers: thermochromic behavior in solution", Organometallics, Vol. 4, pp. 1318-1319, 1985.   DOI
7 L. A. Harrah, and J. M. Zeigler, "Electronic spectra of polysilanes", Macromolecules, Vol. 20, pp. 601-608, 1987.   DOI
8 K. Sakamoto, M. Yoshida, and H. Sakurai, "Highly ordered high-molecular weight alternating polysilylene copolymer prepared by anionic polymerization of masked disilene", Macromolecules, Vol. 23, pp. 4494-4496, 1990.   DOI
9 C. Aitken, J. F. Harrod, and U. S. Gill, "Structural studies of oligosilanes produced by catalytic dehydrogenative coupling of primary organosilanes", Can. J. Chem., Vol. 65, pp. 1804-1809, 1987.   DOI
10 J. F. Harrod and S. S. Yun, "Silyltitanocene complexes as catalysts for the hydrogenation, isomerization, and hydrosilylation of olefins", Organometallics, Vol. 6, pp. 1381-1387, 1987.   DOI
11 C. Aitken, J.-P. Barry, F. Gauvin, J. F. Harrod, A. Malek, and D. Rousseau, "A survey of catalytic activity of. eta. 5-cyclopentadienyl complexes of Groups 4-6 and uranium and thorium for the dehydrocoupling of phenylsilane", Organometallics, Vol. 8, pp. 1732-1736, 1989.   DOI   ScienceOn
12 H.-G. Woo and T. D. Tilley, "$\sigma$-Bond metathesis reactions of Si-H and M-Si bonds. New routes to d0 metal silyl complexes", J. Am. Chem. Soc. Vol. 111, pp. 3757-3758, 1989.   DOI
13 H.-G. Woo and T. D. Tilley, "Dehydrogenative polymerization of silanes to polysilanes by zirconocene and hafnocene catalysts. A new polymerization mechanism" J. Am. Chem. Soc., Vol. 111, pp. 8043-8044, 1989.   DOI
14 J. F. Harrod, "Transformations of organometallics into common and exotic materials; Design and activation", R. M. Laine, Ed., NATO ASI Series E : Appl. Sci. no. 141, Martinus Nijhoff Publishers, Amsterdam, pp. 103, 1988.
15 H.-G. Woo, R. H. Heyn, and T. D. Tilley, "$\sigma$-Bond metathesis reactions for d0 metal-silicon bonds that produce zirconocene and hafnocene hydrosilyl complexes", J. Am. Chem. Soc., Vol. 114, pp. 5698-5707, 1992.   DOI
16 H.-G. Woo, J. F. Walzer, and T. D. Tilley, "Dehydropolymerization of bis-and tris(silyl)arenes to highly crosslinked disilanylenearylene polymers, catalyzed by [($eta.5-C_5H_5$)($eta.5-C_5Me_5$) $ZrH_2]_2$", Macromolecules, Vol. 24, pp. 6863-6866, 1991.   DOI
17 T. Imori, H.-G. Woo, J. F. Walzer, and T. D. Tilley, "Disilanylenearylene oligomers and polymers from dehydropolymerization of 1,4-RH2SiC6H4SiH2R (R= methyl, ethyl, and hexyl)" Chem. Mater., Vol. 12, pp. 1487-1492, 1993.
18 V. K. Dioumaev and J. F. Harrod, "Catalytic dehydrocoupling of phenylsilane with "cation-like" zirconocene derivatives: A new approach to longer silicon chains", Organometallics, Vol. 13, pp. 1548-1550, 1994.   DOI   ScienceOn
19 T. D. Tilley, "The coordination polymerization of silanes to polysilanes by a". sigma.-bond metathesis" mechanism. Implications for linear chain growth", Acc. Chem. Res., Vol. 26, pp. 22-29, 1993.   DOI
20 T. Imori and T. D. Tilley, "The influence of catalyst structure on the dehydropolymerization of phenylsilane", Polyhedron, Vol. 13, pp. 2231-2243, 1994.   DOI   ScienceOn
21 H. G. Woo, S.-Y. Kim, M.-K. Han, E. J. Cho, and I. N. Jung, "Dehydrohomopolymerization and dehydrocopolymerization of new alkylsilanes: synthesis of poly (3-aryl-1-silabutanes)", Organometallics, Vol. 14, pp. 2415-2421, 1995.   DOI   ScienceOn
22 T. Imori, V. Lu, H. Cai, and T. D. Tilley, "Metal-catalyzed dehydropolymerization of secondary stannanes to high molecular weight polystannanes", J. Am. Chem. Soc., Vol. 117, pp. 9939, 1995.
23 W. K. Zou and N.-L. Yang, "Experimental observation of the magnitude and sign of the third order optical nonlinearity in polydibutylstannane", Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.), Vol. 33, pp. 188-189, 1992.
24 L. R. Sita, "A new strategy for the synthesis of homologously pure linear polystannane oligomers", Organometallics, Vol. 11, pp. 1442-1444, 1992.   DOI
25 T. Imori and T. D. Tilley, "High molecular mass polystannanes via dehydropolymerization of di(nbutyl) stannane", J. Chem. Soc., Chem. Commun., pp. 1607, 1993.
26 H.-G. Woo, S.-Y. Kim, W.-G. Kim, E. J. Cho, S. H. Yeon, and I. N. Jung, "Dehydropolymerization of Bis (silyl) alkylbenzenes to Highly Cross-Linked Polysilanes, Catalyzed by Group 4 Metallocene Complex", Bull. Korean Chem. Soc., Vol. 16, pp. 1109-1112, 1995.
27 H.-G. Woo, S.-J. Song, H. You, E. J. Cho, and I. N. Jung, "Catalytic redistribution/ dehydrocoupling of 2-phenyl-1,3-disilapropane by $Cp_2MCl_2$/Red-Al system (M=Ti, Hf)", Bull. Korean Chem. Soc., Vol. 17, pp. 475-478, 1996.   과학기술학회마을
28 T. Nakanishi, J.-I. Nishikawa, Y. Hiromori, H. Yokoyama, M. Koyanagi, S. Takasuga, J.-I. Ishizaki, M. Watanabe, S.-I. Isa, N. Utoguchi, N. Itoh, Y. Kohno, T. Nishihara, and K.Tanaka, "Trialkyltin compounds bind retinoid X receptor to alter human placental endocrine functions", Molecular Endocrinology 2005, Vol. 19, pp. 2502-2516.   DOI   ScienceOn
29 P. T. S. Wong, Y. K. Chau, O. Kramar, and G. A. Bengert, "Structure-toxicity relationship of tin compounds on algae", Canadian J. Fisheries and Aquatic Sci., Vol. 39, pp. 483-488, 1982.   DOI
30 C. Boraiko, and J.Batt, "Evaluation of employee exposure to organic tin compounds used as stabilizers at PVC processing facilities", Tin Stabilizers Association Occup. Environ. Hyg., Vol. 2, pp. 73-76, 2005.   DOI   ScienceOn
31 H.-G. Woo, J.-M. Park, S.-J. Song, S.-Y.Yang, I.-S. Kim, and W.-G. Kim, "Catalytic Dehydropolymerization of Di-n-butylstannane n-Bu2SnH2 by Group 4 and 6 Transition Metal Complexes", Bull. Korean Chem. Soc., Vol. 18, pp. 1291-1295, 1997.   과학기술학회마을
32 R. A. Benkeser, H. Landesman, and D. J. Foster, "The formation of arylsilylpotassium compounds", J. Am. Chem. Soc., Vol. 74, pp. 648-650, 1952..   DOI
33 A. K. Sawyer, "Some reactions of organotin hydrides with organotin oxides and alkoxides", J. Am. Chem. Soc., Vol. 87, pp. 537-539, 1965.   DOI
34 B. Becher, R. J. P. Corriu, C. Guerin, and B. J. L. Henner, "Hypervalent silicon hydrides: evidence for their intermediacy in the exchange reactions of di-and tri-hydrogenosilanes catalysed by hydrides (NaH, KH and $LiAlH_4$)", J. Organomet. Chem., Vol. 369, pp. 147-154, 1989.   DOI   ScienceOn
35 B. Becker, R. Corriu, C. Guerin, and B. Henner, "Catalytic preparation of oligomeric polysilanes", Polym. Prep. (Am. Chem. Soc., Div. Polym. Chem.)., Vol. 56, pp. 854, 1987.
36 R. J. P. Corriu, "Hypervalent species of silicon: structure and reactivity", J. Organomet. Chem., Vol. 400, pp. 81-106, 1990.   DOI   ScienceOn
37 H.-G. Woo, S.-J. Song, E. J. Cho, and I. N. Jung, "Redistribution of bis-and tris(silyl)methanes catalyzed by Red-Al", Bull. Korean Chem. Soc., Vol. 17, pp. 123-124, 1996.
38 H.-G. Woo, Ph.D. Thesis University of California at San Diego, California, 1990.
39 C. Aitken, J. F. Harrod, A. Malek, and E. Samuel, "Oligomerization of phenylgermanes by catalytic dehydrocoupling", J. Organomet. Chem., Vol. 249, pp. 285-291, 1988.
40 J. E. Noh, H.-G. Woo, and H. Cheong, Manuscript in preparation.
41 D. P. Curran and C. T. Chang, "Atom transfer cyclization reactions of ${\alpha}$-iodo carbonyls", Tetrahedron Letts., Vol. 28, pp. 2477-2480, 1987.   DOI   ScienceOn
42 D. P. Curran and M.-H. Chen. "Atom transfer cycloaddition. A facile preparation of functionalized (methylene) cyclopentanes", J. Am. Chem. Soc., Vol. 109, pp. 6558-6560, 1987.   DOI