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Synthesis and Structure of Octamethylcyclo-di(meta-silphenylenesiloxane)

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Abstract

Octamethylcyclo-di(meta-silphenylenesiloxane) 1 (cyclic meta-dimer) was synthesized from 1,3-bis(dimethylhydroxysilyl)benzene 7 in a dilute THF solution, in the presence of a catalytic amount of 4-dimethylaminopyridine (DMAP). In contrast, only small amounts of the cyclic meta-dimer 1, cyclic meta-trimer 2, cyclic meta-tetramer, etc. were obtained when the condensation reaction was carried out with the catalyst n-hexylamine 2-ethylhexoate or sodium hydroxide. The major product in these reactions is polymer 8. The structure of compound 1 was confirmed by X-ray crystallography. This cyclic molecule is most likely unstrained since the X-ray structure reveals that the Si–O–Si bond angle is 142.1(1)° which is similar to that in most unstrained siloxane compounds.

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REFERENCES

  1. (a) P. J. Flory, Principles of Polymer Chemistry (Cornell University Press, Ithaca, 1953); (b) M. Kaftory, M. Kapon, and M. Botoshansky, in The Chemistry of Organic Silicon Compounds Volume 2, Z. Rappoport and Y. Apeloig, eds. (Wiley, New York, 1998), pp. 181–266; (c) O. K. Johannson and C.-L. Lee, in Cyclic Monomers, K. C. Frisch, ed. (Wiley-Interscience, New York, 1972), pp. 459–686; (d) J. Beckmann, K. Jurkschat, U. Kaltenbrunner, N. Pieper, and M. Schurmann, Organometallics 18, 1586 (1999), and references therein.

    Google Scholar 

  2. (a) I. Manners, Angew. Chem. Int. Ed. Engl. 108, 1712 (1996); (b) W. T. Grubb and R. C. Osthoff, J. Am. Chem. Soc. 77, 1405 (1955); (c) J. C. Saam, in Silicon-Based Polymer Science: A Comprehensive Resource, J. M. Zeigler and F. W. G. Fearon, eds. (American Chemical Society, Washington, D.C., 1990), pp. 71–90; (d) J. Chojnowski, in Siloxane Polymers, S. J. Clarson and J. A. Semlyen, eds. (PTR Prentice Hall, Englewood Cliffs, 1993), pp. 1–71.

    Google Scholar 

  3. M. Morton and E. E. Bostick, J. Polym. Sci.: Part A 2, 523 (1964).

    Google Scholar 

  4. M. J. Hunter, J. F. Hyde, E. L. Warrick, and H. J. Fletcher, J. Am. Chem. Soc. 68, 667 (1946).

    Google Scholar 

  5. (a) P. R. Dvornic and R. W. Lenz, High Temperature Siloxane Elastomers (Hüthig & Wepf, Basel, 1990); (b) R. L. Merker and M. J. Scott, J. Polym. Sci.: Part A 2, 15 (1964); (c) L. W. Breed, R. L. Elliott, and M. E. Whitehead, J. Polym. Sci.: Part A-1 5, 2745 (1967); (d) R. E. Burks, Jr., E. R. Covington, M. V. Jackson, and J. E. Curry, J. Polym. Sci., Polym. Chem. Ed. 11, 319 (1973); (e) P. R. Dvornic and R. W. Lenz, J. Polym. Sci., Polym. Chem. Ed. 20, 951 (1982); (f) N. Koid and R. W. Lenz, J. Polym. Sci., Polym. Symp. 70, 91 (1983); (g) J. E. Mark and B. Erman, Rubberlike Elasticity: A Molecular Primer (John Wiley & Sons, New York, 1988).

    Google Scholar 

  6. R. Zhang, A. R. Pinhas, and J. E. Mark, Macromolecules 30, 2513 (1997).

    Google Scholar 

  7. G. H. Barnes, Jr. and N. E. Daughenbaugh, J. Org. Chem. 31, 885 (1966).

    Google Scholar 

  8. J. F. Hyde, U.S. Pat. 3,160,601 (Dec. 8, 1964).

  9. (a) R. J. Smith, R. A. Capaldi, D. Muchmore, and F. Dahlquist, Biochemistry 17, 3719 (1978). (b) B. Neises and W. Steglich, Angew. Chem. Int. Ed. Engl. 17, 522 (1978).

    Google Scholar 

  10. (a) F. E. Ziegler and G. D. Berger, Synth. Commun. 539 (1979); (b) C. Gilon, Y. Klausner, and A. Hassner, Tetrahedron Lett. 3811 (1979).

  11. E. D. Lipp and A. L. Smith, in The Analytical Chemistry of Silicones, A. L. Smith, ed. (Wiley, Neck York, 1991), pp. 305–346.

    Google Scholar 

  12. R. Zhang, Ph. D. Thesis (University of Cincinnati, Cincinnati, OH, 1999).

  13. Siemens SHELXTL-PC Manual, Release 4.1, Siemens Analytical Instruments (Madison, WI, 1990).

  14. M. R. Churchill, Inorg. Chem. 12, 1213 (1973).

    Google Scholar 

  15. International Tables for Crystallography, Kluwer Academic Publishers (Dordrecht, The Netherlands, 1995), Vol. C, pp. 713–791.

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Zhang, R., Pinhas, A.R., Mark, J.E. et al. Synthesis and Structure of Octamethylcyclo-di(meta-silphenylenesiloxane). Journal of Inorganic and Organometallic Polymers 9, 63–77 (1999). https://doi.org/10.1023/A:1021483115907

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  • DOI: https://doi.org/10.1023/A:1021483115907

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