Skip to main content
SpringerLink
Log in

1-Methyl-1-Vinyl-3,3,5,5-Tetraphenylcyclotrisiloxane: An Organofunctional Cyclotrisiloxane

  • Communication
  • Published:
Journal of Inorganic and Organometallic Polymers and Materials Aims and scope Submit manuscript

Abstract

The characterization of 1-methyl-1-vinyl-3,3,5,5-tetraphenylcyclotrisiloxane by NMR(1H,13C,29Si) and X-ray crystallography is reported. The central siloxane ring is planar with Si–O bond lengths and angles which are similar to those found in the structures of other cyclotrisiloxanes. There is significant thermal motion of the methyl and vinyl groups. Very low incorporation of the siloxane is observed in the radical catalyzed copolymerization of the siloxane with styrene.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1

References

  1. H.R. Allcock, Chemistry and Applications of Polyphosphazenes (Wiley-Interscience, Hoboken, New Jersey, 2003)

    Google Scholar 

  2. V. Chandrasekhar, Inorganic and Organometallic Polymers (Springer-Verlag, Heildelberg, 2005)

    Google Scholar 

  3. C.W. Allen, Trends Polym. Sci. 2, 342 (1994)

    CAS  Google Scholar 

  4. J.C. van de Grampel, in Synthesis and Characterization of Poly(organophosphazenes), Chapter 7, ed. by M. Gleria, R. DeJaeger (Nova Science Publishers, New York, 2004)

    Google Scholar 

  5. L. McNally, C.W. Allen, Heteroatom. Chem. 4, 159 (1993)

    Article  CAS  Google Scholar 

  6. J. Schwab, J. Lichtenhan, J. Appl. Organomet. Chem. 12, 707 (1998)

    Article  CAS  Google Scholar 

  7. A.A. Zhdanov, B.G. Zavin, O.G. Blokhina, Vysokomol. Soedin. Ser. B 25, 582 (1983)

    CAS  Google Scholar 

  8. K.A. Andrianov, O.G. Blokhina, B.G. Zavin, N.V. Pertsova, Vysokomol. Soedin. Ser. A 19, 434 (1997)

    Google Scholar 

  9. R.C. Sporck, U.S. Patent, US 3340287 (1967)

  10. P.I. Prescott, T.G. Selin, U.S. Patent, US 3222369, 1965

  11. C.N. Myer, C.W. Allen, J. Inorg. Organomet. Polym. Mater. 17, 143 (2007)

    Article  CAS  Google Scholar 

  12. XSCANS. X-ray Single Crystal Analysis System. Version 2.1., Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, 1994

  13. G.M. Sheldrick, SHELXTL/PC User’s Manual. Siemens Analytical X-ray Instruments Inc (Madison, Wisconsin, 1990)

    Google Scholar 

  14. G.M. Sheldrick, SHELX193 Program for the Refinement of Crystals Structures (University of Göttingen, Germany, 1993)

    Google Scholar 

  15. U. Wannagat, G. Bogedian, A. Schervan, H.C. Marsmann, D.J. Brauer, H. Bürger, F. Dörrenbach, G. Pawelke, C. Krüger, K.-H. Claus, Z. Naturforsch 45b, 931 (1991)

    Google Scholar 

  16. R. Pomes-Hernandez, Y. Smolin, Y. Shepelev, Rev. Cubana Fis. 2, 153 (1982)

    CAS  Google Scholar 

  17. G. Pyronel, Atti Accad. Naz. Lincei 16, 231 (1954)

    Google Scholar 

  18. R.P. Hernandez, Acta Crystallogr. Sect. A: Cryst. Phys. Diffr. Theor. Crystallogr. 34, S406 (1978)

    Article  Google Scholar 

  19. W. Clegg, Acta Crystallogr. Sect. B: Struct. Crystallogr. Cryst. Chem. 38, 1648 (1982)

    Article  Google Scholar 

  20. H.-W. Lerner, S. Scholz, N. Wiberg, K. Polborn, M. Bolte, M. Wagner, Z. Anorg. Allg. Chem. 631, 1863 (2005)

    Article  CAS  Google Scholar 

  21. Yu.E. Ovchinnikov, Yu.T. Struchkov, M.I. Buzin, V.S. Papkov, Vysokomol. Soedin Ser. B 39, 430 (1997)

    CAS  Google Scholar 

  22. B. Ziemer, M. Bacher, N. Auner, N. Act. Cryst. C54, 1111 (1998)

    Article  CAS  Google Scholar 

  23. P.E. Tomlins, J.E. Lydon, D. Akrigg, B. Sheldrick, Acta Crystallogr. Sect. C: Cryst. Struct. Commun. 41, 292 (1985)

    Article  Google Scholar 

  24. J.F. Hyde, L.K. Frevel, H.S. Nutting, P.S. Petrie, M.A. Purcell, J. Am. Chem. Soc. 69, 488 (1947)

    Article  CAS  Google Scholar 

  25. N.G. Bokii, G.N. Zakharova, Y.T. Struchkov, Zh. Strukt. Khim 13, 291 (1972)

    CAS  Google Scholar 

  26. Y.E. Ovchinnikov, V.E. Shklover, Y.T. Struchkov, L.M. Tartakovskaya, N.G. Vasilenko, A.A. Zhdanov, Metalloorg. Khim 1, 1126 (1988)

    Google Scholar 

  27. A.A. Ahdab, G. Rima, H. Gornitzka, J. Barrau, J. Organomet. Chem. 658, 94 (2002)

    Article  Google Scholar 

  28. M.J. MacLachlan, J. Zheng, A.J. Lough, I. Manners, C. Mordas, R. LeSuer, W.E. Geiger, L.M. Liable-Sands, A.L. Rheingold, Organomet 18, 1337 (1999)

    Article  CAS  Google Scholar 

  29. O.I. Cherenkova, N.V. Alekseev, A.I. Gusev, J. Struct. Chem. 16, 504 (1975)

    CAS  Google Scholar 

  30. V.E. Shklover, N.G. Bokii, Y.T. Struchkov, K.A. Andianov, B.G. Zavin, V.S. Svistunov, J. Struct. Chem. 15, 841 (1974)

    Article  CAS  Google Scholar 

  31. D. Schmidt-Böse, U. Klingebiel, Chem. Ber. 123, 449 (1990)

    Article  Google Scholar 

  32. T. Buschen, W. Dietz, U. Klingebiel, M. Noltemeyer, Y. Schwerdtfeger, Z. Naturforsch. B: Chem. Sci. 62, 1358 (2007)

    Google Scholar 

  33. Y. Itami, B. Marciniec, M. Kubicki, Organometallics 22, 3717 (2003)

    Article  CAS  Google Scholar 

  34. R. Gewald, U. Scheim, K. Ruhlmann, H. Goesman, D. Fenske, J. Organomet. Chem. 450, 73 (1993)

    Article  CAS  Google Scholar 

  35. S.T. Malinovsky, A.T. Vallina, H. Stoeckli-Evans, Zh. Strukt. Khim 47, 1143 (2006)

    Google Scholar 

  36. M. Seno, M. Hasegawa, T. Hirano, T. Sato, J. Polym. Sci. A: Polym. Chem. 43, 5864 (2005)

    Article  CAS  Google Scholar 

  37. J.G. DuPont, C.W. Allen, Macromolecules 12, 169 (1979)

    Article  CAS  Google Scholar 

  38. C.W. Allen, R.P. Bright, Macromolecules 19, 571 (1986)

    Article  CAS  Google Scholar 

  39. M.A. Hempenius, R.G.H. Lammerink, G.J. Vansco, Macromolecules 30, 266 (1997)

    Article  CAS  Google Scholar 

Download references

Acknowledgment

The authors would like to thank Vermont EPSCoR for financial support of this project.

Author information

Author notes

  1. Chip Nataro

    Present address: Department of Chemistry, Lafayette College, Easton, PA, 18042, USA

Authors and Affiliations

  1. Department of Chemistry, University of Vermont, Burlington, VT, 05405-0125, USA

    Chip Nataro, William M. Cleaver & Christopher W. Allen

Authors
  1. Chip Nataro
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. William M. Cleaver
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Christopher W. Allen
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Christopher W. Allen.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Nataro, C., Cleaver, W.M. & Allen, C.W. 1-Methyl-1-Vinyl-3,3,5,5-Tetraphenylcyclotrisiloxane: An Organofunctional Cyclotrisiloxane. J Inorg Organomet Polym 19, 566–569 (2009). https://doi.org/10.1007/s10904-009-9300-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10904-009-9300-x

Keywords

Search

Navigation